DE2148203A1 - Verfahren zur Herstellung einer Ntert.-Butoxycarbonylaminosäure - Google Patents
Verfahren zur Herstellung einer Ntert.-ButoxycarbonylaminosäureInfo
- Publication number
- DE2148203A1 DE2148203A1 DE19712148203 DE2148203A DE2148203A1 DE 2148203 A1 DE2148203 A1 DE 2148203A1 DE 19712148203 DE19712148203 DE 19712148203 DE 2148203 A DE2148203 A DE 2148203A DE 2148203 A1 DE2148203 A1 DE 2148203A1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- reaction
- butyl
- acid
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 239000002253 acid Substances 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 9
- 229940024606 amino acid Drugs 0.000 claims description 52
- 150000001413 amino acids Chemical class 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- -1 N-tert-butoxycarbonylamino Chemical group 0.000 claims description 20
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 18
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- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 10
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- GHBAYRBVXCRIHT-VIFPVBQESA-N S-benzyl-L-cysteine zwitterion Chemical compound OC(=O)[C@@H](N)CSCC1=CC=CC=C1 GHBAYRBVXCRIHT-VIFPVBQESA-N 0.000 claims description 4
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- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 claims description 2
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- IFGCUJZIWBUILZ-UHFFFAOYSA-N sodium 2-[[2-[[hydroxy-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid Chemical compound [Na+].C=1NC2=CC=CC=C2C=1CC(C(O)=O)NC(=O)C(CC(C)C)NP(O)(=O)OC1OC(C)C(O)C(O)C1O IFGCUJZIWBUILZ-UHFFFAOYSA-N 0.000 claims description 2
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- 239000007790 solid phase Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960002898 threonine Drugs 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8079770A | 1970-10-14 | 1970-10-14 | |
| US00157606A US3855238A (en) | 1970-10-14 | 1971-06-28 | Process for preparing n-tertiary-butoxycarbonyl amino acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2148203A1 true DE2148203A1 (de) | 1972-04-20 |
Family
ID=26763943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712148203 Pending DE2148203A1 (de) | 1970-10-14 | 1971-09-27 | Verfahren zur Herstellung einer Ntert.-Butoxycarbonylaminosäure |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3855238A (Direct) |
| CH (1) | CH538450A (Direct) |
| DE (1) | DE2148203A1 (Direct) |
| FR (1) | FR2111290A5 (Direct) |
| GB (1) | GB1348438A (Direct) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038306A (en) * | 1967-08-07 | 1977-07-26 | Merck & Co., Inc. | N-t-butoxycarbonyl-s-lower alkanoylamidomethyl-cysteine and p-nitrophenyl esters |
| US3936452A (en) * | 1971-09-17 | 1976-02-03 | Nitto Boseki Co., Ltd. | Process of producing pyrimidyl thiocarbonates |
| US4087417A (en) * | 1976-09-15 | 1978-05-02 | Parke, Davis & Company | Hexapeptides and methods for their production |
| US4085096A (en) * | 1976-09-15 | 1978-04-18 | Parke, Davis & Company | Hexapeptides and methods for their production |
| DK36584A (da) * | 1983-02-15 | 1984-08-16 | Hoffmann La Roche | Imidazolderivater |
| WO1994008947A1 (fr) * | 1992-10-15 | 1994-04-28 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Nouveau derive aminoacide |
| US5798387A (en) * | 1992-10-15 | 1998-08-25 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Amino acid derivatives |
| US7147878B2 (en) * | 2002-04-26 | 2006-12-12 | University Of Kentucky Research Foundation | Modified soy products and methods for reducing odor and improving flavor of soy products |
| US8664361B2 (en) * | 2002-04-26 | 2014-03-04 | University Of Kentucky Research Foundation | Soy products with reduced levels of sulfite, free radicals and methanethiol |
| CN108101811A (zh) | 2016-11-25 | 2018-06-01 | 斯福瑞（南通）制药有限公司 | 生产n-叔丁氧羰基-2-氨基-3,3-二甲基丁酸的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH427841A (de) * | 1959-08-24 | 1967-01-15 | Ciba Geigy | Verfahren zur Herstellung von a-(w-Aminoalkyl)-a-aminoessigsäuregruppenhaltigen Peptiden |
| US3325466A (en) * | 1961-01-11 | 1967-06-13 | American Cyanamid Co | Tertiary butyl group as a carboxyl protecting group in the synthesis of peptides |
| GB1166403A (en) * | 1967-07-21 | 1969-10-08 | Ici Ltd | Process for the manufacture of Amino Acid Derivatives |
| US3609164A (en) * | 1968-03-27 | 1971-09-28 | Tanabe Seiyaku Co | Process for preparing {11 -butoxycarbonyl compounds |
-
1971
- 1971-06-28 US US00157606A patent/US3855238A/en not_active Expired - Lifetime
- 1971-09-27 DE DE19712148203 patent/DE2148203A1/de active Pending
- 1971-10-07 GB GB4669171A patent/GB1348438A/en not_active Expired
- 1971-10-13 CH CH1493171A patent/CH538450A/fr not_active IP Right Cessation
- 1971-10-13 FR FR7136706A patent/FR2111290A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3855238A (en) | 1974-12-17 |
| GB1348438A (en) | 1974-03-20 |
| FR2111290A5 (Direct) | 1972-06-02 |
| CH538450A (fr) | 1973-06-30 |
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