Methanol → (5S,8S)-3-(3-chlorophenyl)-7-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylic acid

HRID 2038564

반응식

HRID 2038564 반응식
C[O:2][C:3]([C@@H:5]1[CH2:21][C@:8]2([O:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)[CH2:9]2)[CH2:7][N:6]1[C:22](=[O:37])[C@@H:23]([NH:28][C:29]([O:31][CH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:30])[C:24]([CH3:27])([CH3:26])[CH3:25])=[O:4].[Li+].[OH-].CO>C1COCC1>[Cl:20][C:16]1[CH:15]=[C:14]([N:10]2[CH2:9][C@@:8]3([CH2:21][C@@H:5]([C:3]([OH:4])=[O:2])[N:6]([C:22](=[O:37])[C@@H:23]([NH:28][C:29]([O:31][CH:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)=[O:30])[C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:7]3)[O:12][C:11]2=[O:13])[CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59547346(5S,8S)-methyl-3-(3-chlorophenyl)-7-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate

생성물 1

HCID 59547318(5S,8S)-3-(3-chlorophenyl)-7-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylic acid수율 46.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(5S,8S)-methyl-3-(3-chlorophenyl)-7-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylate (C3) (22 mg, 41 μmol, 1 eq.) was diluted with dry THF (0.5 mL) then 1 M LiOH (82 μL, 82 μmol, 2 eq.) and MeOH (20 μL) was added. The reaction was stirred overnight at room temp. and concentrated to give 10 mg (19 μmol) of (5S,8S)-3-(3-chlorophenyl)-7-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-8-carboxylic acid (D3). LC MS+: 522.35 at 3.14 min (10-90%, 3-5 min, Formic Acid).

후처리

  1. concentrationconcentrated

출처 및 근거

ORD 기록
ord-59d921abbb714fa48c34ebcddc60dcf4
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575208B2

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