Triethylamine → t-Butyl 2-hydroxy-2-[(3R,4R)-3-phenylacetamido-4-[(RS)-tetrahydropyran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetate

HRID 1421788노트

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HRID 1421788 반응식
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[C@@H:14]([S:15][CH2:16][C:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)=[O:18])[NH:13][C:12]2=[O:25])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])[CH:27]=[O:28].C(N(CC)CC)C.C(OCC)(=O)C>ClCCCl>[OH:28][CH:27]([N:13]1[C@H:14]([S:15][CH2:16][C:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[O:18])[C@H:11]([NH:10][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:12]1=[O:25])[C:26]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10986247Tert-butyl 2-oxoacetateHCID 18396289(3R,4R)-3-Phenylacetamido-4-[(RS)-tetrahydropyran-2-yl-carbonylmethylthio]azetidin-2-one

생성물 1

HCID 18397160t-Butyl 2-hydroxy-2-[(3R,4R)-3-phenylacetamido-4-[(RS)-tetrahydropyran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetate수율 82%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

실험 절차

(3R,4R)-3-Phenylacetamido-4-[(RS)-tetrahydropyran-2-yl-carbonylmethylthio]azetidin-2-one (1.7 g) in 1,2-dichloroethane (20 ml) was successively treated with 0.5M t-butyl glyoxylate in 1,2-dichlorethane (10 ml) and triethylamine (50 mg, 70 μl) and monitored by t.l.c. (ethyl acetate) until no starting material remained. The reaction mixture was concentrated and flash chromatography (70% ethyl acetate in hexane, ethyl acetate) to afford the title compound as a yellow foam (1.9 g, 82%); νmax (CH2Cl3) 3400 (w), 1780, 1736, 1687 cm-1 ; δH (CDCl3) 1.49 (9H, s) overlapping 1.44-1.61 (4H, m), 1.8-2.0 (2H, m), 3.35-3.58 (3H, m), 3.65 (2H, s), 3.81-3.92 (1H, m), 4.01-4.06 (1H, m), 4.28-4.43 (1H, m), 4.99, 5.00, 5.07 (together 1H, 3d, J4.7 Hz), 5.21, 5.32, 5.33 (together 1H, 3d, J6.8, 7.7, 7.6 Hz), 5.42, 5.50 (together 1H, 2dd, J4.8, 8.7 Hz, 6.35, 6.36, 6.61 (together 1H, 3d, J8.7 Hz) and 7.27-7.38 (5H, m).

후처리

  1. concentrationThe reaction mixture was concentrated

출처 및 근거

ORD 기록
ord-3519d2157cec4acd902cf4f6a800a75c
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077952

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