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Acetic Acid → (3S)-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid

HRID 1396941
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HRID 1396941 반응식
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=[O:17])[NH:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[CH:28]([N:30]([CH2:39][C@@H:40]([CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:41](F)=[O:42])[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:29].CC(O)=O>CN(C=O)C>[CH:28]([N:30]([CH2:39][C@@H:40]([CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:41]([N:12]1[C@H:13]([C:16]([OH:18])=[O:17])[CH2:14][CH2:15][N:11]1[C:9]([O:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:10])=[O:42])[O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:29]
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참가 물질

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반응물 4

HCID 176Acetic AcidHCID 81531Diisopropylethylamine2회HCID 537448401-(Benzyloxy carbonyl)pyrazolidine-3-carboxylic acidHCID 86706374(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl fluoride

생성물 1

HCID 86706375(3S)-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid
수율 35%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a 50 mL round-bottomed flask was added 1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (3.00 g, 8.23 mmol) and Hunig's base (DIPEA) (4.41 mL, 25.3 mmol) in DMF (15 mL). To this mixture was added (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl fluoride (1.87 g, 6.33 mmol) in DMF (5 mL) dropwise. The reaction mixture was stirred at room temperature overnight, then was stored in refrigerator for two days. HOAc (3 ml) was added to neutralize the excess Hunig's base. The resulting solution was purified by RP-HPLC to provide (3S)-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid as a white solid (1.153 g, 35%). LCMS: (M+H)+: 526.0.

후처리

  1. waitwas stored in refrigerator for two days
  2. customThe resulting solution was purified by RP-HPLC

출처 및 근거

ORD 기록
ord-3b94aaab4b05410995e60305efdb0c87
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901119B2

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