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Triethylamine → (S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid benzyl ester

HRID 1970488
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HRID 1970488 반응식
[CH2:1]([O:8][C:9](=[O:23])[C@@H:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:12][CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][C:25]([Si:28](Cl)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:27])[CH3:26].C(N(CC)CC)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9](=[O:23])[C@@H:10]([NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:11][CH2:12][CH2:13][O:14][Si:28]([C:25]([CH3:27])([CH3:26])[CH3:24])([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 11056397(S)-Benzyl 2-((tert-butoxycarbonyl)amino)-5-hydroxypentanoate

생성물 1

HCID 66854935(S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid benzyl ester

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6228
Dimethylformamide
용매

실험 절차

To a solution of 2.5 g (S)-2-tert-Butoxycarbonylamino-5-hydroxy-pentanoic acid benzyl ester (prepared by adapting the procedure described by Diederichsen et al., Org. Biomol. Chem., 2005, 3, 1058) in 50 ml DMF were added 2.0 ml TBDPSCl, 1.2 ml triethylamine and 95 mg DMAP and the resulting suspension was stirred for 4 days. The solvent was evaporated, the residue dissolved in ethyl acetate and washed with aqueous LiCl (4 w/w), 0.1 M HCl and saturated NaHCO3. The crude product obtained after evaporation of the solvent was purified by chromatography on silica using heptane/ethyl acetate 12/1 as eluent. Yield: 2.0 g colorless oil.

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with aqueous LiCl (4 w/w), 0.1 M HCl and saturated NaHCO3

출처 및 근거

ORD 기록
ord-0c9d88b28b5440678ebc7878f3d04a87
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08426420B2

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