Dicyclohexylcarbodiimide → 1-[(t-Butoxycarbonylamino)acetamido]-2-(2-fluorobenzoyl)pyrrole

HRID 280123Notes

Reaction equation

HRID 280123 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[F:14].[C:16]([O:20][C:21]([NH:23][CH2:24][C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:16]([O:20][C:21]([NH:23][CH2:24][C:25]([NH:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[F:14])=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 134577161-Amino-2-(2-fluorobenzoyl)pyrrole

Product 1

HCID 134577471-[(t-Butoxycarbonylamino)acetamido]-2-(2-fluorobenzoyl)pyrroleYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 1-amino-2-(2-fluorobenzoyl)pyrrole (25.8 g, 0.126 mol) and N-(tert-butoxycarbonyl)glycine (22.4 g, 0.128 mol) in 300 ml of dichloromethane was added dicyclohexylcarbodiimide (26.4 g, 0.128 mmol) in two portions over 3 minutes. The reaction mixture was stirred at ambient temperature for 2 hours and then filtered. The filtrate was evaporated to an oil which was purified by HPLC (silica gel, 4:3 hexane-ethyl acetate) to give 37.2 g (82%) of crystals, m.p. 114°-116°.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to an oil which
  3. customwas purified by HPLC (silica gel, 4:3 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5c3ef1ff31dd4b6ea0edebb3e359cc47
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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