1,2-Dichloroethane → Boc-Cys(StBu)-Gly-OCH3

HRID 1055261노트

반응식

HRID 1055261 반응식
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][S:4][S:5][C:6]([CH3:9])([CH3:8])[CH3:7].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.[CH3:42][O:43][C:44](=[O:47])[CH2:45][NH2:46]>ClCCl.CCOC(C)=O>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([NH:46][CH2:45][C:44]([O:43][CH3:42])=[O:47])=[O:12])[CH2:3][S:4][S:5][C:6]([CH3:7])([CH3:8])[CH3:9]

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 122755Glycine methyl ester hydrochlorideHCID 14258343N-((1,1-dimethylethoxy)carbonyl)-3-((1,1-dimethylethyl)dithio)-L-alanine

생성물 1

HCID 14334607Boc-Cys(StBu)-Gly-OCH3수율 89%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

N-Boc-Cys(StBu)-OH 9 (1.00 g, 3.23 mmol) was dissolved in dry dichloromethane (25 mL) followed by the addition of EDC (0.75 g, 3.87 mmol), HOBt (0.53 g, 3.87 mmol), NMM (1.77 mL, 16.15 mmol) and glycine methyl ester hydrochloride (0.61 g, 4.84 mmol) at 0° C. under argon. The reaction mixture was then allowed to warm to room temperature and stirred overnight. After evaporation of solvent, the residue obtained was taken in EtOAc (35 mL), washed with 20% citric acid solution (2 30 mL), sat. NaHCO3 (20 mL), brine and dried over MgSO4. The EtOAc layer was evaporated in vacuo and resulting crude product was purified by flash silica gel column chromatography to get the dipeptide product 12 as white foam (1.09 g, 89% yield). 1H NMR (300 MHz, CDCl3) δ7.35, 5.81 (2H), 4.44 (1H), 3.82 (2H), 3.61 (3H), 3.02-2.83 (2H), 1.43, 1.28 (18H); 13C NMR (75 MHz, CDCl3) δ171.2, 169.9, 155.5, 80.0, 53.5, 52.3, 48.0, 41.4, 37.9, 30.0, 28.5; ESI-LRMS m/z 380.5 (M+H)+.

후처리

  1. customAfter evaporation of solvent
  2. customthe residue obtained
  3. washwashed with 20% citric acid solution (2 30 mL), sat. NaHCO3 (20 mL), brine
  4. dry with materialdried over MgSO4
  5. customThe EtOAc layer was evaporated in vacuo
  6. customresulting crude product
  7. customwas purified by flash silica gel column chromatography

출처 및 근거

ORD 기록
ord-287a9219e46348b59c5236a34e0ee9c6
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394338B2

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