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

HRID 1421788ノート

反応式

HRID 1421788 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

実験手順

(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).

後処理

  1. concentrationThe reaction mixture was concentrated

出典と根拠

ORDレコード
ord-3519d2157cec4acd902cf4f6a800a75c
出典データセット
uspto-grants-2000_06
特許番号
US06077952

反応ノート

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