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Triethylamine → 4-Methoxybenzyl (RS)-2-hydroxy-2-[4-[(2RS,5SR)-5-methoxycarbonyltetrahydrofuran-2-ylcarbonylmethylthio)-3-phenylacetamidoazetidin-2-on-1-yl]acetate

HRID 376605
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HRID 376605 반응식
O.[C:2]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)(=[O:5])[CH:3]=[O:4].[CH3:16][O:17][C:18]([CH:20]1[O:24][CH:23]([C:25]([CH2:27][S:28][C@H:29]2[NH:32][C:31](=[O:33])[C@H:30]2[NH:34][C:35](=[O:43])[CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:26])[CH2:22][CH2:21]1)=[O:19].C(N(CC)CC)C>ClC(Cl)C>[OH:4][CH:3]([N:32]1[CH:29]([S:28][CH2:27][C:25]([CH:23]2[CH2:22][CH2:21][CH:20]([C:18]([O:17][CH3:16])=[O:19])[O:24]2)=[O:26])[CH:30]([NH:34][C:35](=[O:43])[CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:31]1=[O:33])[C:2]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)=[O:5]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 18780117HCID 18780117, 화합물HCID 67907703(3R,4R)-4-[(2RS,5SR)-5-Methoxycarbonyltetrahydrofuran-2-ylcarbonylmethylthio)-3-phenylacetamidoazetidin-2-one

생성물 1

HCID 867551044-Methoxybenzyl (RS)-2-hydroxy-2-[4-[(2RS,5SR)-5-methoxycarbonyltetrahydrofuran-2-ylcarbonylmethylthio)-3-phenylacetamidoazetidin-2-on-1-yl]acetate

시약·촉매·용매 1

HCID 6365
1,1-Dichloroethane
용매
2회

실험 절차

4-Methoxybenzyl glyoxylate hydrate (1.50g) in dichloroethane (30ml) was heated at reflux for 1h using a Dean and Stark apparatus for heavy entrainers. The mixture was cooled to room temperature and then a solution of (3R,4R)-4-[(2RS,5SR)-5-methoxycarbonyltetrahydrofuran-2-ylcarbonylmethylthio]-3-phenylacetamidoazetidin-2-one (2.208g) in dichloroethane (20ml) was added followed by triethylamine (0.1ml). The mixture was stirred at room temperature for 1h and then the solvents were evaporated. The title compound was obtained as a mixture of isomers (2.66g) by column chromatography of the residue using gradient elution (silica gel, 1:1 hexane:ethyl acetate going to neat ethyl acetate); vmax (CHCl3) 3412, 1776, 1741 and 1681cm-1.

후처리

  1. customthe solvents were evaporated

출처 및 근거

ORD 기록
ord-62ac6919c7854f63b50569930f2b5273
출처 데이터셋
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06020329

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