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HRID29149

反应详情

EQUATION

反应方程式

HRID 29149 的结构方程式

REACTANTS

反应物

2
结构：CS(=O)(=O)Nc1nc2ccc(S(=O)(=O)Cl)cc2[nH]1
HCID22997016

未命名化合物

结构：CC(C)ONC[C@@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C
HCID86592444

未命名化合物

PRODUCTS

生成物

1
结构：CC(C)OC(NS(=O)(=O)c1ccc2nc(NS(C)(=O)=O)[nH]c2c1)[C@H](O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C
HCID86592443

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
结构：c1ccncc1
溶剂HCID1049

Pyridine

C5H5N

PROCEDURE

实验过程

tert-Butyl-N-((1S,2R)-1-benzyl-3-(isopropyloxy)amino-2-hydroxypropyl)carbamate (86 mg, 0.25 mmol) was combined with 2-[(methylsulfonyl)amino]benzimidazol-5-ylsulfonyl chloride (77 mg, 0.25 mmol) in anhydrous pyridine (1 ml) with a catalytic amount of N,N-dimethylaminopyridine. The reaction was stirred at room temperature overnight. The solvent was evaporated under vacuum. The crude mixture was diluted in EtOAc and washed with water and brine. Organic phase was dried with MgSO4 and solvent was removed in vacuo. Purification by TLC prep (2% MeOH/CH2Cl2). Recovered 56 mg (37%) of product as a white solid. HPLC showed the material to be 98% pure; Ret. time=9.87 min. 1H NMR (CDCl3): 7.12-8.04 (m, 8H), 6.5 (m, 1H), 4.47-4.51 (m, 2H), 3.68 (m, 2H), 3.22 (s, 3H), 2.81-2.88 (m, 3H), 1.75 (m, 2H), 1.22 (s, 9H), 1.16 (d, 6H). MS (ES+): obs. M+H@ 612.1 amu.

WORKUP

后处理

  1. customThe solvent was evaporated under vacuum
  2. additionThe crude mixture was diluted in EtOAc
  3. washwashed with water and brine
  4. dry with materialOrganic phase was dried with MgSO4 and solvent
  5. customwas removed in vacuo
  6. customPurification by TLC prep (2% MeOH/CH2Cl2)
  7. customRecovered 56 mg (37%) of product as a white solid