(2S,4R) Fmoc-4-amino-1-boc-pyrrolidine-2-carboxylic acid → 4-Amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

HRID 606661노트

반응식

HRID 606661 반응식
[C:1]([C@@:18]1(C(O)=O)[CH2:22][C@@H:21]([NH2:23])[CH2:20][N:19]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([O:3]CC1C2C(=CC=CC=2)C2C1=CC=CC=2)=[O:2]>C(#N)C.N1CCCC1>[NH2:23][CH:21]1[CH2:20][N:19]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH:18]([C:1]([OH:3])=[O:2])[CH2:22]1

참가 물질

4

반응물 1

HCID 67068446(2S,4R) Fmoc-4-amino-1-boc-pyrrolidine-2-carboxylic acid

생성물 1

HCID 41840634-Amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid수율 40%

시약·촉매·용매 2

HCID 31268Pyrrolidine촉매HCID 6342Acetonitrile용매

실험 절차

To a solution of (2S,4R) Fmoc-4-amino-1-boc-pyrrolidine-2-carboxylic acid (400 mg, 0.884 mmol) in acetonitrile (15 mL), five drops of pyrrolidine was added. The reaction mixture was stirred at rt for 3 hr. Then it was concentrated and put on high vacuum to give crude 4-amino-1-boc-pyrrolidine-2-carboxylic acid. In another round-bottomed flask, a solution of Pd2dba3 (40 mg, 5% mol) and racemic-BINAP (56 mg, 10% mol) was stirred under nitrogen in degassed toluene (8 mL) at rt for 1 h. Then 1-chloroisoquinoline (216 mg, 1.326 mmol) and sodium t-butoxide (340 mg, 3.536 mmol) were added and the reaction mixture was stirred for 30 min. Then 4-amino-1-boc-pyrrolidine-2-carboxylic acid was added and the reaction mixture was heated under reflux for 1 h. Water was added to quench the reaction and the aqueous layer was separated and filtered through filter paper. It was then concentrated and purified by Prep. HPLC to give coupled product as TFA salt. (165 mg, 40% yield)

후처리

  1. concentrationThen it was concentrated

출처 및 근거

ORD 기록
ord-094cca7f05854d148b79ad1ac1a55f32
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915291B2

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