Dicyclohexylcarbodiimide → (R)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate

HRID 1080455Notes

Reaction equation

HRID 1080455 reaction equation
[C:1]([NH:11][C@@H:12]([C:14]([OH:16])=O)[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[NH2:17][N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:5]1([CH2:4][O:3][C:1](=[O:2])[NH:11][C@H:12]([CH3:13])[C:14](=[O:16])[NH:17][N:18]2[CH:22]=[CH:21][CH:20]=[CH:19]2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 70832N-Cbz-d-alanineHCID 1365891-Aminopyrrole

Product 1

HCID 131718294(R)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamateYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution consisting of carbobenzyloxy-D-alanine (10.0 g) and N-aminopyrrole (3.68 g) in dry DCM (224 ml) was added DCC (9.71 g) at 0° C. under nitrogen. The cooling bath was removed after ten minutes and the reaction mixture was allowed to stir at room temperature for 24 hours. The suspension was filtered and the DCU filter cake was washed with hot ethyl acetate. Concentration of the filtrate gave the crude product. Recrystallization from EtOAc/hexane afforded 11.69 g of the desired product as a solid, m.p. 172°-174° C.

Workup

  1. customThe cooling bath was removed after ten minutes
  2. filtrationThe suspension was filtered
  3. filtrationthe DCU filter cake
  4. washwas washed with hot ethyl acetate
  5. customConcentration of the filtrate gave the crude product
  6. customRecrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-71916879153d41678db08766e065461d
Source dataset
uspto-grants-1996_12
Patent number
US05580987

Reaction notes

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