HRID1778346

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID4311764

Sodium borohydride (Na(BH4))

H4BNa

结构：COC(=O)c1c(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ccc(-c2ccoc2C=O)c1OS(=O)(=O)c1ccc(C)cc1

HCID86684729

未命名化合物

2 次

PRODUCTS

生成物

HCID86684728

未命名化合物

收率 97.6%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID702

Ethanol

C2H6O

PROCEDURE

实验过程

Sodium borohydride (0.304 g) was added to a solution of methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-(2-formylfuran-3-yl)-2-(4-methylbenzenesulfonyloxy)-benzoate (Intermediate 22, 3.9 g) in ethanol (50 mL) and the mixture was stirred for 15 minutes. The mixture was evaporated to dryness and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give methyl 6-[bis-(tert-butoxycarbonyl)amino]-3-(2-hydroxymethylfuran-3-yl)-2-(4-methylbenzene-sulfonyloxy)-benzoate (3.82 g) as a white solid.

WORKUP

后处理

customThe mixture was evaporated to dryness
customthe residue was partitioned between ethyl acetate and water
customThe organic layer was separated
dry with materialdried (Na2SO4)
filtrationfiltered
customThe filtrate was evaporated to dryness

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-71574d8d05eb434a909ee6eb6a750c46
来源数据集: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09266896B2
来源说明: uspto-grants-2016_02

反应 SMILES

[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:11]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:14]([C:32]2[CH:36]=[CH:35][O:34][C:33]=2[CH:37]=[O:38])=[CH:13][CH:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C(O)C>[C:42]([O:41][C:39]([N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[C:11]1[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:14]([C:32]2[CH:36]=[CH:35][O:34][C:33]=2[CH2:37][OH:38])=[CH:13][CH:12]=1)=[O:40])([CH3:44])([CH3:45])[CH3:43]