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HRID658522

反应详情

EQUATION

反应方程式

HRID 658522 的结构方程式

REACTANTS

反应物

4
结构：O
HCID962

Water

H2O

结构：O=[N+]([O-])c1ccc(S(=O)(=O)Cl)cc1
HCID7404

Benzenesulfonyl chloride, 4-nitro-

C6H4ClNO4S

结构：CCN(CC)CC
HCID8471

Triethylamine

C6H15N

结构：CC(C)CNC[C@@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C
HCID9902339

tert-Butyl {(2S,3R)-3-hydroxy-4-[(2-methylpropyl)amino]-1-phenylbutan-2-yl}carbamate

C19H32N2O3

PRODUCTS

生成物

1
结构：CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)S(=O)(=O)c1ccc([N+](=O)[O-])cc1
HCID10279676

tert-Butyl {(2S,3R)-3-hydroxy-4-[(2-methylpropyl)(4-nitrobenzene-1-sulfonyl)amino]-1-phenylbutan-2-yl}carbamate

C25H35N3O7S

收率 96.5%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC(C)O
溶剂HCID3776

Isopropanol

C3H8O

CONDITIONS

反应条件

温度
62.5 °C

PROCEDURE

实验过程

7.5 g (22.3 mmol) of (1S,2R)-(1-benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid tert-butyl ester and 2.7 g (26.8 mmol, 1.2 equiv) of triethylamine are dissolved in 100 g of isopropanol and heated to 60-65° C. 5.41 g (24.5 mmol, 1.1 eq) p-nitrophenyl-sulfonyl chloride are added in several portions within 30 minutes. The reaction mixture is kept at 60° C. for another 30 minutes. 10 g of water are added and the suspension is stirred for an additional 30 minutes at 60° C. The mixture is cooled to 25° C. within 90 min and the product is filtered off, washed with a mixture of isopropanol/water (1:1 v/v) and dried under vacuum to yield 11.23 g (96.5%) of white (1S,2R)-{1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-carbamic acid tert-butyl ester.

WORKUP

后处理

  1. temperatureThe mixture is cooled to 25° C. within 90 min
  2. filtrationthe product is filtered off
  3. washwashed with a mixture of isopropanol/water (1:1 v/v)
  4. customdried under vacuum