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Diisopropylethylamine → 2-(trimethylsilyl)ethyl (S)-2-((R)-3-((R)-(3-chlorophenyl)(2-oxopropoxy)methyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate

HRID 451918
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HRID 451918 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:14]2[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]2)[O:9][CH2:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.[CH:20]1([CH2:26][C@H:27]([NH:40][C:41](=O)[O:42]C2C=CC([N+]([O-])=O)=CC=2)[CH2:28][N:29]([CH3:39])[C:30]([O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:31])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([O:9][CH2:10][C:11](=[O:13])[CH3:12])[C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:41]([NH:40][C@@H:27]([CH2:26][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[CH2:28][N:29]([CH3:39])[C:30](=[O:31])[O:32][CH2:33][CH2:34][Si:35]([CH3:37])([CH3:38])[CH3:36])=[O:42])[CH2:15]2)[CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 592017501-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)propan-2-oneHCID 59382919(S)-4-nitrophenyl 1-cyclohexyl-3-(methyl((2-(trimethylsilyl)ethoxy)carbonyl)amino)propan-2-ylcarbamate

생성물 1

HCID 866394602-(trimethylsilyl)ethyl (S)-2-((R)-3-((R)-(3-chlorophenyl)(2-oxopropoxy)methyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate수율 11.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 1-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)propan-2-one, obtained as described above, (S)-4-nitrophenyl 1-cyclohexyl-3-(methyl((2-(trimethylsilyl)ethoxy)carbonyl)amino)propan-2-ylcarbamate (0.390 g, 0.81 mmol), and DIPEA (2.5 mL) in CH2Cl2 was stirred at rt for 16 h. After the reaction mixture was evaporated under reduced pressure, the crude product was purified by reversed-phase HPLC to afford 0.0487 g (11.4% in three steps) of 2-(trimethylsilyl)ethyl (S)-2-((R)-3-((R)-(3-chlorophenyl)(2-oxopropoxy)methyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate. MS ESI +ve m/z 624 (M+H).

후처리

  1. customobtained
  2. customAfter the reaction mixture was evaporated under reduced pressure
  3. customthe crude product was purified by reversed-phase HPLC

출처 및 근거

ORD 기록
ord-84281c0fb28c46e6b32422a6ed6c57bc
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08487108B2

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