Benzoyl chloride → (3-Benzoylamino-propyl)-carbamic acid tert-butyl ester

HRID 14805

Reaction equation

HRID 14805 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH2:11])([CH3:4])([CH3:3])[CH3:2].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 10492863(3-Benzoylamino-propyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-Amino-propyl)-carbamic acid tert-butyl ester (1.6 g) was treated with with benzoyl choride (1.1 eq.) and triethylamine (1.5 eq) in methylene chloride (50 mL). The reaction mixture was washed with 1 N HCl, sat, NaHCO3, and sat NaCl and the solvent removed to give product. LC-MS showed the product had the expected M+H+ of 279.

Workup

  1. washThe reaction mixture was washed with 1 N HCl
  2. customthe solvent removed
  3. customto give product

Sources & evidence

ORD record
ord-28cac14ad73544c99a6be09cbbe020e9
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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