2-Aminophenol → 867353-53-5

HRID 2354140Notes

Reaction equation

HRID 2354140 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11](=[O:13])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 10868DicyclohexylcarbodiimideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanine

Product 1

HCID 51284468867353-53-5

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-tert-Butoxycarbonylamino-propionic acid (5-1) (1.0 g, 5.3 mmol) and 2-aminophenol (5-2) (578 mg, 5.3 mmol) in dichloromethane (10 mL) was added N,N′-dicyclo hexyl carbodiimide (1.3 g, 6.4 mmol). The resulting mixture was stirred at room temperature overnight. The volatile solvents were removed by rotovap evaporation then the reaction mixture was directly purified by silica gel chromatography (10-100% Hexane/Ethyl Acetate) to recover the desired product (5-3) as white solid: 1H-NMR (500 MHz, d4-CD3OD) δ7.43 (m, 1H), 6.88 (m, 1H), 6.76 (m, 1H), 6.70 (m, 1H), 3.29 (m, 2H), 2.48 (m, 2H), 1.29 (s, 9H).

Workup

  1. customThe volatile solvents were removed by rotovap evaporation
  2. customthe reaction mixture was directly purified by silica gel chromatography (10-100% Hexane/Ethyl Acetate)
  3. customto recover the desired product (5-3) as white solid

Sources & evidence

ORD record
ord-f3dfb09129fc459fa6c9223fc23796ab
Source dataset
uspto-grants-2010_07
Patent number
US07750151B2

Reaction notes

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