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Dichloromethane → 3-methoxy-2,2-dimethyl-3-oxopropyl (3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate

HRID 732700
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HRID 732700 반응식
ClCCl.O=C1CCC(=O)N1[O:11][C:12]([O:14][CH2:15][C:16]([CH3:22])([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=O.OCC(C)(C)C(OC)=O.[C:32]1([C@H:42]([N:44]([CH2:52][C@@H:53]2[C@@H:57]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[CH2:56][NH:55][CH2:54]2)[C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[CH3:43])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1>C(N(CC)CC)C>[C:47]([O:46][C:45]([N:44]([CH2:52][C@@H:53]1[C@@H:57]([C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[CH2:56][N:55]([C:12]([O:14][CH2:15][C:16]([CH3:22])([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=[O:11])[CH2:54]1)[C@@H:42]([C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1)[CH3:43])=[O:51])([CH3:49])([CH3:50])[CH3:48]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6344Dichloromethane2회HCID 84152Methyl 3-hydroxypivalateHCID 86628525tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamateHCID 86628559Methyl 3-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}oxy)-2,2-dimethylpropionate

생성물 1

HCID 86628558
3-methoxy-2,2-dimethyl-3-oxopropyl (3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

A 2 ml dichloromethane solution of methyl 3-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}oxy)-2,2-dimethylpropionate prepared from 136 mg of methyl 3-hydroxy-2,2-dimethylpropionate in the same manner as in Reference Example 46 was added to 5 ml dichloromethane solution of 235 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate and 0.21 ml of triethylamine. After 12Hours of stirring at room temperature, the reaction solution was concentrated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (hexane-ethyl acetate) to obtain 227 mg of 3-methoxy-2,2-dimethyl-3-oxopropyl (3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate as a colorless amorphous substance.

후처리

  1. concentrationthe reaction solution was concentrated under a reduced pressure
  2. customthe thus obtained residue was purified by a silica gel column chromatography (hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-862bb5e985b24741848c401502531de8
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07585886B2

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