HRID653060

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14797

Potassium hydroxide

HKO

HCID85955

Dibenzo[b,k][1,4,7,10,13,16]hexaoxacyclooctadecin, eicosahydro-

C20H36O6

HCID527610

Allyl bromoacetate

C5H7BrO2

结构：C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N[C@@H]1SC(c1ccccc1)(c1ccccc1)c1ccccc1

HCID13821375

未命名化合物

PRODUCTS

生成物

结构：C=CCOC(=O)CN1C(=O)[C@H]([C@@H](C)O[Si](C)(C)C(C)(C)C)[C@H]1SC(c1ccccc1)(c1ccccc1)c1ccccc1

HCID11114682

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID241

Benzene

C6H6

PROCEDURE

实验过程

The tritylthioazetidinone 2 is treated with 1.5 equivalents of allyl bromoacetate and powdered potassium hydroxide in benzene solvent at ambient temperature in the presence of dicyclohexyl-18-crown-6 for 4 hours. The resulting (3S,4R)-1-(allyloxycarbonyl)methyl-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-4-triphenylmethylthio-2-azetidinone (3) is isolated by conventional means. Alternatively p-nitro-benzylbromoacetate may be substituted for allylbromoacetate.

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-6912df3c3d144ff483c04ed34633bf5d
来源数据集: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04675317
来源说明: uspto-grants-1987_06

反应 SMILES

[C:1]1([C:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[S:8][C@H:9]2[NH:12][C:11](=[O:13])[C@@H:10]2[C@H:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:37][C:38]([O:40][CH2:41][CH:42]=[CH2:43])=[O:39].[OH-].[K+].C1CC2OCCOCCOC3C(OCCOCCOC2CC1)CCCC3>C1C=CC=CC=1>[CH2:41]([O:40][C:38]([CH2:37][N:12]1[C@H:9]([S:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:10]([C@H:14]([O:16][Si:17]([C:20]([CH3:22])([CH3:23])[CH3:21])([CH3:19])[CH3:18])[CH3:15])[C:11]1=[O:13])=[O:39])[CH:42]=[CH2:43]