JP6744669B2 - 水酸基を配向基とするエステルからアミドへの変換触媒 - Google Patents
水酸基を配向基とするエステルからアミドへの変換触媒 Download PDFInfo
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- JP6744669B2 JP6744669B2 JP2018519528A JP2018519528A JP6744669B2 JP 6744669 B2 JP6744669 B2 JP 6744669B2 JP 2018519528 A JP2018519528 A JP 2018519528A JP 2018519528 A JP2018519528 A JP 2018519528A JP 6744669 B2 JP6744669 B2 JP 6744669B2
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- 0 C*C(C(*)(*)C(*)(C(*)=O)Cl)(O)[Re] Chemical compound C*C(C(*)(*)C(*)(C(*)=O)Cl)(O)[Re] 0.000 description 2
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Description
項1. 元素周期律表の第4族または第5族の遷移金属化合物を含む触媒の存在下に、α−ヒドロキシエステル化合物、β−ヒドロキシエステル化合物、γ−ヒドロキシエステル化合物、及びδ−ヒドロキシエステル化合物からなる群より選択される少なくとも1種のヒドロキシエステル化合物と、アミノ化合物とを反応させて、前記ヒドロキシエステル化合物のα位、β位、γ位、またはδ位にヒドロキシル基を有するエステル基をアミド化する、ヒドロキシエステル化合物のアミド化反応法。
項2. 前記ヒドロキシエステル化合物が、下記一般式(1a)〜(1d)で表されるヒドロキシエステル化合物である、項1に記載のヒドロキシエステル化合物のアミド化反応法。
項3. 前記アミノ化合物が、下記一般式(3)で表されるアミノ化合物である、項1または2に記載のヒドロキシエステル化合物のアミド化反応法。
項4. 前記遷移金属化合物が、チタン化合物、ジルコニウム化合物、ハフニウム化合物、バナジウム化合物、ニオブ化合物、及びタンタル化合物からなる群より選択される少なくとも1種である、項1〜3のいずれかに記載のヒドロキシエステル化合物のアミド化反応法。
項5. 前記ヒドロキシエステル化合物を100mol%とした場合に、前記触媒の使用量が、100mol%以下である、項1〜4のいずれかに記載のヒドロキシエステル化合物のアミド化反応法。
項6. アミド化反応は、有機溶媒中、反応温度0℃〜150℃、反応時間10分〜72時間の条件で行われる、項1〜5のいずれかに記載のヒドロキシエステル化合物のアミド化反応法。
項7. 前記ヒドロキシエステル化合物が、α−ヒドロキシエステル、β−ヒドロキシエステル、γ−ヒドロキシエステル、またはδ−ヒドロキシエステルとは異なるエステル基をさらに有している、項1〜6のいずれかに記載のヒドロキシエステル化合物のアミド化反応法。
項8. 前記アミノ化合物が、アミノ酸もしくはその塩、又はアミノ酸エステルもしくはその塩である、項1〜7のいずれかに記載のヒドロキシエステル化合物のアミド化反応法。
項9. 前記ヒドロキシエステル化合物が、アミノ基を有している、項1〜8のいずれかに記載のヒドロキシエステル化合物のアミド化反応法。
項10. 前記ヒドロキシエステル化合物及び前記アミノ化合物の少なくとも一方が、アミノ酸残基を2以上有するオリゴペプチドである、項1〜9のいずれかに記載のヒドロキシエステル化合物のアミド化反応法。
項11. アミド化反応で得られるアミド化合物が、下記一般式(4a)〜(4d)からなる群より選択される少なくとも1種である、項1〜10のいずれかに記載のアミド化合物の製造方法。
項12. 元素周期律表の第4族または第5族の遷移金属化合物を含む触媒であって、
α−ヒドロキシエステル化合物、β−ヒドロキシエステル化合物、γ−ヒドロキシエステル化合物、及びδ−ヒドロキシエステル化合物からなる群より選択される少なくとも1種のヒドロキシエステル化合物と、アミノ化合物とを反応させて、前記ヒドロキシエステル化合物のα位、β位、γ位、またはδ位にヒドロキシル基を有するエステル基をアミド化する、ヒドロキシエステル化合物のアミド化反応法に用いるための触媒。
下記式に示すように、室温(約23℃)下、トルエン溶媒中において、24時間、表1に示す遷移金属化合物(10 mol%)の存在下、β−ヒドロキシプロピオン酸フェニル(1a)1モル当量とパラトルイジン(3a)3モル当量とを共存させて、これらのアミド化反応を行った。その際、水酸基を有しないプロピオン酸フェニル(2a)1モル当量を反応系中に共存させることで、アミド化反応の化学選択性を評価した。結果を表1に示す。
次に、下記式に示すように、室温(約23℃)または100℃下、トルエン溶媒1 mL中において、24時間、Ta(OEt)5触媒(10mol%)の存在下、β−ヒドロキシエステル(1)0.25mmolと各種アミノ化合物(3) 0.75mmolとを共存させて、これらのアミド化反応を行った。表2に、得られた生成物の化学式と収率を示す。表2の収率(yield)は、単離収率である。なお、実施例1と同様、β位の水酸基が水素原子であること以外はβ−ヒドロキシエステル(1)と同じ構造を有するカルボン酸エステル(2)0.25mmolを反応系中に共存させることで、アミド化反応の化学選択性を評価した。式中のβ−ヒドロキシエステル(1)の基R1は、表2に記載のとおりである。また、各種アミノ化合物(3)の基R2及びR3は、それぞれ、表2に記載の生成物のアミノ化合物に結合している基(カルボニル基とは異なる基)に対応している。
下記式に示すように、室温(23℃)または100℃下、トルエン溶媒(1mL)中において、Ta(OEt)5触媒(10 mol%)の存在下、24時間、β位に置換基を有する各種のβ−ヒドロキシエステル(1)0.25mmolと、各種アミノ化合物(3)0.75mmolとを共存させて、これらのアミド化反応を行った。表3に、得られた生成物の化学式と収率を示す。表3の収率(yield)は、単離収率である。なお、実施例1と同様、水酸基を含まないこと以外はβ−ヒドロキシエステル(1)と同じ構造を有するカルボン酸エステル(2)0.25mmolを反応系中に共存させることで、アミド化反応の化学選択性を評価した。また、式中のβ−ヒドロキシエステル(1)の基R1、R2は、それぞれ、表3に記載の生成物の前記β位に結合している基に対応している。また、式中のβ−ヒドロキシエステル(1)の基R3は、表3に記載のとおりである。各種アミノ化合物(3)の基R4は、それぞれ、表3に記載の生成物のアミノ化合物に結合している基(水酸基及びカルボニル基とは異なる基)に対応している。
下記式に示すように、それぞれ、100℃下または60℃下、トルエン溶媒(1mL)中において、24時間、Ta(OEt)5触媒(10mol%)の存在下、分子内にエステル基を2つ有する化合物(6a、6b)0.25mmolと、ベンジルアミン(3n)0.75mmolとを共存させて、これらのアミド化反応を行った。下記式中に、得られた生成物の化学式と収率を示す。
下記式に示すように、60〜100℃下、トルエン溶媒(1mL)中において、Ta(OEt)5触媒(10mol%)の存在下、24時間、各種アミノ酸エステル(8)0.25mmolとアミノ化合物(9)0.75mmolとを共存させ、これらのアミド化反応を行った。表4に、得られた生成物の化学式、収率、及びジアステレオ選択率(dr)を示す。式中の各種アミノ酸エステル(8)の基R1は、表4に記載の生成物のβ位に結合している基に対応している。アミノ化合物(9)の基R2についても、それぞれ、表4に記載の生成物に結合している基に対応している。
下記式(6−1)〜(6−7)に示すように、室温(23℃)または100℃下、トルエン溶媒(1mL)中において、Ta(OEt)5触媒(10mol%)の存在下、エステル基のα位、β位、γ位、またはδ位に水酸基を有する各種のヒドロキシエステル(1当量)と、各種アミノ化合物(3.0当量)とを共存させて、これらのアミド化反応を行った。なお、下記式示すように、実施例1と同様、水酸基を含まないエステル化合物を反応系中に共存させて、アミド化反応の化学選択性を評価した反応(式(6−1)、(6−2)、(6−4)、(6−5))、さらに、β−ヒドロキシエステル化合物とδ−ヒドロキシエステル化合物とを共存させた反応(式(6−6))も行った。なお、式(6−7)には、ヒドロキシエステルの式中のnが0、3、4である場合をまとめて記載している。各式中に、得られた生成物の化学式と収率を示す。
下記式に示すように、室温(23℃)下、トルエン溶媒(1mL)中において、Ta(OEt)5触媒(10mol%)の存在下、ベンジルオキシカルボニル基(Cbz)でアミノ基が保護されたL−セリンメチルエステル(Cbz−L−Ser−OMe)(すなわち、β−ヒドロキシエステル)1.0当量と、L−セリンとL−アラニンとのジペプチドのt−ブチルエステル(すなわち、アミノ化合物)1.1当量とを共存させて、100℃で18時間、アミド化反応を行った。その結果、下記式で示されるトリペプチドが得られた(収率50%)
下記式に示すように、室温(23℃)下、トルエン溶媒(1mL)中において、Ta(OEt)5触媒(10mol%)の存在下、ベンジルオキシカルボニル基(Cbz)でアミノ基が保護されたL−セリンプロパルギルエステル(Cbz−L−Ser−OCH2CCH)(すなわち、β−ヒドロキシエステル)1.0当量と、L−セリンとL−アラニンとのジペプチドのt−ブチルエステル(すなわち、アミノ化合物)1.1当量とを共存させて、60℃で42時間、アミド化反応を行った。その結果、下記式で示されるトリペプチドが得られた(収率72%)
下記式に示すように、室温(23℃)下、溶媒(1−3mL)中において、Ta(OEt)5触媒(10mol%)の存在下、β−ヒドロキシエステルとしてのベンジルオキシカルボニル基(Cbz)でアミノ基が保護されたトリペプチドメチルエステル11(すなわち、β−ヒドロキシエステル)1.0当量と、アミノ化合物としてのL−アラニンとL−フェニルアラニンとのジペプチドのt−ブチルエステル12(すなわち、アミノ化合物)2−3当量とを共存させて、60℃で24時間、アミド化反応を行った。その結果、下記式で示されるオリゴペプチド13(アミノ酸5量体の誘導体)が得られた。収率を表5に示す。
下記式に示すように、室温(23℃)下、メタノール溶媒(0.3mL)中において、触媒(100mol%)の存在下、下記式のβ−ヒドロキシエステル14(AcHN−Ala−Phe−Val−Ala−Thr−COOMe)1.0当量と、アミノ化合物15(H2N−Ala−Phe−COOtBu)2.0当量とを共存させて、60℃で24時間、アミド化反応を行った。その結果、下記式で示されるオリゴペプチド16(アミノ酸7量体の誘導体)が得られた。収率を表6に示す。
下記式に示すように、室温(23℃)下、無溶媒、または溶媒(0.3mL)中において、触媒(100mol%)の存在下、下記式のβ−ヒドロキシエステル14(AcHN−Ala−Phe−Val−Ala−Thr−COOMe)1.0当量と、アミノ化合物17(H2N−Ala−Phe−Ile−COOBn)2.0当量とを共存させて、60℃で24時間、アミド化反応を行った。その結果、下記式で示されるオリゴペプチド18(アミノ酸8量体の誘導体)が得られた。収率を表7に示す。
Claims (8)
- 触媒の存在下に、少なくとも1種のβ−ヒドロキシアミノ酸エステル化合物と、アミノ酸もしくはその塩又はそのエステルとを反応させて、前記β−ヒドロキシアミノ酸エステル化合物のβ位にヒドロキシル基を有するエステル基を、前記アミノ酸もしくはその塩又はそのエステルのアミノ基によりアミド化することを含む、ヒドロキシアミノ酸エステル化合物のアミド化反応法であって、
前記触媒が、
TaX1 5(但し、5つのX1は、それぞれ独立に、アルコキシ基又はハロゲン原子を表す。)で表されるタンタル化合物、
NbX2 5(但し、5つのX2は、それぞれ独立に、アルコキシ基を表す。)で表されるニオブ化合物、
VOX3 3(但し、5つのX3は、それぞれ独立に、アルコキシ基を表す。)で表されるバナジウム化合物、
TiX4 4(但し、4つのX4は、それぞれ独立に、アルコキシ基を表す。)で表されるチタン化合物、
ZrX5 4(但し、4つのX5は、それぞれ独立に、アルコキシ基を表す。)で表されるジルコニウム化合物、及び
HfX6 4(但し、4つのX6は、それぞれ独立に、アルコキシ基を表す。)で表されるハフニウム化合物
から選択される少なくとも1種の遷移金属化合物を含む、ヒドロキシアミノ酸エステル化合物のアミド化反応法。 - 前記β−ヒドロキシアミノ酸エステル化合物が、アラニン、アルギニン、アスパラギン、アスパラギン酸、システイン、グルタミン、グルタミン酸、グリシン、ヒスチジン、イソロイシン、ロイシン、リシン、メチオニン、フェニルアラニン、プロリン、セリン、トレオニン、トリプトファン、チロシン、及びバリン、並びにこれらのうち少なくとも1種を含むアミノ酸多量体から選択されるアミノ酸のエステルがβ−ヒドロキシ化されてなるβ−ヒドロキシアミノ酸エステルである、請求項1に記載のヒドロキシアミノ酸エステル化合物のアミド化反応法。
- 前記アミノ酸もしくはその塩又はそのエステルが、アラニン、アルギニン、アスパラギン、アスパラギン酸、システイン、グルタミン、グルタミン酸、グリシン、ヒスチジン、イソロイシン、ロイシン、リシン、メチオニン、フェニルアラニン、プロリン、セリン、トレオニン、トリプトファン、チロシン、及びバリン、並びにこれらのうち少なくとも1種を含むアミノ酸多量体から選択されるアミノ酸もしくはその塩又はそのエステルである、請求項1または2に記載のヒドロキシアミノ酸エステル化合物のアミド化反応法。
- 前記β−ヒドロキシアミノ酸エステル化合物を100mol%とした場合に、前記触媒の使用量が、100mol%以下である、請求項1〜3のいずれか一項に記載のヒドロキシアミノ酸エステル化合物のアミド化反応法。
- アミド化反応は、有機溶媒中、反応温度0℃〜150℃、反応時間10分〜72時間の条件で行われる、請求項1〜4のいずれか一項に記載のヒドロキシアミノ酸エステル化合物のアミド化反応法。
- 前記β−ヒドロキシアミノ酸エステル化合物が、β−ヒドロキシエステル基とは異なる第2のエステル基をさらに有すると共に、前記第2のエステル基のα位、β位、γ位、及びδ位にはヒドロキシ基が存在しない、請求項1〜5のいずれか一項に記載のヒドロキシアミノ酸エステル化合物のアミド化反応法。
- 前記β−ヒドロキシアミノ酸エステル化合物及び前記アミノ酸もしくはその塩又はそのエステルの少なくとも一方が、アミノ酸残基を2以上有するオリゴペプチドである、請求項1〜6のいずれか一項に記載のヒドロキシアミノ酸エステル化合物のアミド化反応法。
- 少なくとも1種のβ−ヒドロキシアミノ酸エステル化合物と、アミノ酸もしくはその塩又はそのエステルとを反応させて、前記β−ヒドロキシアミノ酸エステル化合物のβ位にヒドロキシル基を有するエステル基を、前記アミノ酸もしくはその塩又はそのエステルのアミノ基によりアミド化することを含む、ヒドロキシアミノ酸エステル化合物のアミド化反応法に用いるための触媒であって、
TaX1 5(但し、5つのX1は、それぞれ独立に、アルコキシ基又はハロゲン原子を表す。)で表されるタンタル化合物、
NbX2 5(但し、5つのX2は、それぞれ独立に、アルコキシ基を表す。)で表されるニオブ化合物、
VOX3 3(但し、5つのX3は、それぞれ独立に、アルコキシ基を表す。)で表されるバナジウム化合物、
TiX4 4(但し、4つのX4は、それぞれ独立に、アルコキシ基を表す。)で表されるチタン化合物、
ZrX5 4(但し、4つのX5は、それぞれ独立に、アルコキシ基を表す。)で表されるジルコニウム化合物、及び
HfX6 4(但し、4つのX6は、それぞれ独立に、アルコキシ基を表す。)で表されるハフニウム化合物
から選択される少なくとも1種の遷移金属化合物を含む、触媒。
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