JP2003160546A5 - - Google Patents

Info

Publication number

JP2003160546A5

JP2003160546A5 JP2001360835A JP2001360835A JP2003160546A5 JP 2003160546 A5 JP2003160546 A5 JP 2003160546A5 JP 2001360835 A JP2001360835 A JP 2001360835A JP 2001360835 A JP2001360835 A JP 2001360835A JP 2003160546 A5 JP2003160546 A5 JP 2003160546A5

Authority

JP

Japan

Prior art keywords

trans

amino

cyclopentanol

methylbenzyl

succinate

Prior art date

2001-11-27

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.)

Granted

Links

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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 40
• XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 31
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
• 239000013078 crystal Substances 0.000 description 16
• KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 16
• RMRXNEDPUBVWOA-UHFFFAOYSA-N C(CCC(=O)O)(=O)O.C1(CCCC1)O Chemical compound C(CCC(=O)O)(=O)O.C1(CCCC1)O RMRXNEDPUBVWOA-UHFFFAOYSA-N 0.000 description 8
• 150000003839 salts Chemical class 0.000 description 8
• 239000001384 succinic acid Substances 0.000 description 8
• 239000000203 mixture Substances 0.000 description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
• DTNJEMPCYVPJNY-KPXBVGPJSA-N butanedioic acid (1R,2R)-2-[[(1R)-1-phenylethyl]amino]cyclopentan-1-ol Chemical compound OC(=O)CCC(O)=O.N([C@H](C)C=1C=CC=CC=1)[C@@H]1CCC[C@H]1O DTNJEMPCYVPJNY-KPXBVGPJSA-N 0.000 description 4
• 238000001556 precipitation Methods 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• DTNJEMPCYVPJNY-JJZGMWGRSA-N C(CCC(=O)O)(=O)O.C[C@@H](C1=CC=CC=C1)N[C@H]1[C@@H](CCC1)O Chemical compound C(CCC(=O)O)(=O)O.C[C@@H](C1=CC=CC=C1)N[C@H]1[C@@H](CCC1)O DTNJEMPCYVPJNY-JJZGMWGRSA-N 0.000 description 3
• 238000006243 chemical reaction Methods 0.000 description 3
• 239000012452 mother liquor Substances 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 239000000543 intermediate Substances 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 125000006178 methyl benzyl group Chemical group 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• 150000003890 succinate salts Chemical class 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
• 235000020357 syrup Nutrition 0.000 description 2
• XRTOQDRFDAUSLY-CYZMBNFOSA-N (1r,2r)-2-[[(1s)-1-phenylethyl]amino]cyclopentan-1-ol Chemical compound N([C@@H](C)C=1C=CC=CC=1)[C@@H]1CCC[C@H]1O XRTOQDRFDAUSLY-CYZMBNFOSA-N 0.000 description 1
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 238000012824 chemical production Methods 0.000 description 1
• 238000000034 method Methods 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• -1 α-methylbenzyl group Chemical group 0.000 description 1