Acetic Acid → (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid

HRID 1396938노트

반응식

HRID 1396938 반응식
[NH:1]1[CH:5]([C:6]([OH:8])=[O:7])[CH2:4][CH:3]=[N:2]1.[CH:9]1([CH2:14][C@H:15]([CH2:19][N:20]([CH:29]=[O:30])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16](F)=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10]1.CCN(C(C)C)C(C)C.CC(O)=O>C(Cl)Cl>[CH:9]1([CH2:14][C@H:15]([CH2:19][N:20]([CH:29]=[O:30])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]([N:1]2[C@H:5]([C:6]([OH:8])=[O:7])[CH2:4][CH:3]=[N:2]2)=[O:17])[CH2:13][CH2:12][CH2:11][CH2:10]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 128798564,5-dihydro-1H-pyrazole-5-carboxylic acidHCID 86706340(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl fluoride

생성물 1

HCID 86706370(5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid수율 46%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

4,5-Dihydro-1H-pyrazole-5-carboxylic acid (1.273 g, 11.16 mmol) in 26.6 mL of DCM was added into a solution of (2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl fluoride (4.12 g, 13.39 mmol) in 30 mL of DCM, and followed by Hunig's base (5.83 ml, 33.5 mmol). The resulting solution was stirred at ambient temperature for 2 hrs. HOAc (10 ml) was added to neutralize the solution, and then the solvent was removed to give a crude product which was purified by RP-HPLC to give (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-4,5-dihydro-1H-pyrazole-5-carboxylic acid (1.03 g, 2.57 mmol, 46% yield). MS (ES+) m/z 401.9 (MH+).

후처리

  1. customthe solvent was removed
  2. customto give a crude product which
  3. customwas purified by RP-HPLC

출처 및 근거

ORD 기록
ord-77ecbd6380cf47c18068ce782c7b6c34
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901119B2

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