Triethylamine → (3-Chloro-4-methanesulfonylamino-5-vinylbenzyl)carbamic Acid tert-butyl Ester

HRID 2358382Notes

Reaction equation

HRID 2358382 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[C:12]([NH2:17])=[C:11]([Cl:18])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[C:12]([NH:17][S:21]([CH3:20])(=[O:23])=[O:22])=[C:11]([Cl:18])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68456355(4-Amino-3-chloro-5-vinylbenzyl)carbamic acid tert-butyl ester

Product 1

HCID 68456846(3-Chloro-4-methanesulfonylamino-5-vinylbenzyl)carbamic Acid tert-butyl EsterYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Amino-3-chloro-5-vinylbenzyl)carbamic acid tert-butyl ester (40.2 mg, 0.14 mmol), methanesulfonyl chloride (5 eq, 0.71 mmol, 55.15 μl), and triethylamine (3 eq, 0.42 mmol, 58.34 μl) were added in methylene chloride. The reaction mixture was stirred for 5 hr. The reaction mixture was purified with similar procedure to step 5 of Example 8 to obtain a title compound (30.7 mg, 59.83%).

Workup

  1. customThe reaction mixture was purified with similar procedure to step 5 of Example 8

Sources & evidence

ORD record
ord-23a8ff67468749bcbc721f217bf51e11
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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