HRID1649342

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID14798

Sodium Hydroxide

HNaO

2 次

HCID562787

4-Methoxy-2,3,6-trimethylbenzenesulfonyl chloride

C10H13ClO3S

结构：CC(C)(C)OC(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)OCc1ccccc1

HCID10318477

未命名化合物

PRODUCTS

生成物

结构：COc1cc(C)c(S(=O)(=O)n2cc(C[C@H](NC(=O)OC(C)(C)C)C(=O)O)c3ccccc32)c(C)c1C

HCID131713226

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID8154

未命名化合物

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

In the same manner as Example 5, Boc-Trp-OBzl (1.97 g, 5 mM) was reacted with 4-methoxy-2,3,6-trimethylbenzene-sulfonyl chloride (1.87 g, 7.5 mM) in dichloromethane in the presence of sodium hydroxide (500 mg, 12.5 mM) and cetyltrimethylammonium chloride (16 mg, 0.05 mM). The reaction product was then hydrolyzed with an aqueous solution of sodium hydroxide to give Boc-Trp(Mtr)-OH. Yield 2.05 g (79.4%); m.p. 78°-80° C.; [α]D22 -24.8° (c=0.5, DMF).

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-0b5fe27e35054174b77b9a62de3e7338
来源数据集: uspto-grants-1983_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04416820
来源说明: uspto-grants-1983_11

反应 SMILES

[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:13]([O:15]CC1C=CC=CC=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:30][O:31][C:32]1[CH:37]=[C:36]([CH3:38])[C:35]([S:39](Cl)(=[O:41])=[O:40])=[C:34]([CH3:43])[C:33]=1[CH3:44].[OH-].[Na+]>ClCCl.[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC>[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:39]([C:35]2[C:34]([CH3:43])=[C:33]([CH3:44])[C:32]([O:31][CH3:30])=[CH:37][C:36]=2[CH3:38])(=[O:41])=[O:40])[CH:5]=1