1-Hydroxybenzotriazole → {(S)-2-[benzyloxylimino-methyl-pyrrolidine-1-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester

HRID 222515노트

반응식

HRID 222515 반응식
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:16]([OH:18])=O)[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])[CH3:3].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[CH2:38]([O:45][N:46]=[CH:47][CH:48]1[CH2:52][CH2:51][CH2:50][NH:49]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>ClCCl>[C:2]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[C:16]([N:49]1[CH2:50][CH2:51][C:47](=[N:46][O:45][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:48]1[CH3:52])=[O:18])([CH3:1])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7004938N-(tert-Butoxycarbonyl)-L-cyclohexylglycineHCID 72562396Pyrrolidine-2-carbaldehyde-O-benzyl-oxime

생성물 1

HCID 86623471{(S)-2-[benzyloxylimino-methyl-pyrrolidine-1-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

The solution of boc-L-α-cyclohexylglycine (1.27 g, 4.92 mmole), 1-hydroxylbenzotriazole (0.99 g, 7.38 mmole), diisopropylethylamine (2.54 g, 19.68 mmole), and O-benzotriazole-N,N,N,N-tetramethyl-urounium hexafluorophosphate (2.80 g, 7.38 mmole) in dichloromethane (30 ml) is stirred for 15 minutes at room temperature. A solution of pyrrolidine-2-carbaldehyde-O-benzyl-oxime (˜1.00 g, 0.49 mmole) in dichloromethane is added. The reaction solution is stirred for three hours at room temperature and then quenched with saturated NaHCO3 aqueous., extracted with dichloromethane. The organic layer is combined, dried, and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; from 20% to 70% of ethyl acetate in hexane) to provide 1.81 g (83% over 2 steps) of the title compound. M+H+=444.2

후처리

  1. customquenched with saturated NaHCO3 aqueous
  2. extraction, extracted with dichloromethane
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe residue is purified by flash chromatography (silica gel; from 20% to 70% of ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-8e8a9b47b6bc4575b70ec1b0b88c040d
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207183B2

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