Dicyclohexylcarbodiimide → (+/-)-Phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate

HRID 22377

Reaction equation

HRID 22377 reaction equation
[C:1]([NH:11][CH: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][CH: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 95657N-(Benzyloxycarbonyl)-DL-alanineHCID 1365891-Aminopyrrole

Product 1

HCID 19973168(+/-)-Phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamateYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution consisting of carbobenzyloxy-D,L-alanine (10.0 g) and N-aminopyrrole (3.68 g) in dry DCM (224 ml) was added DCC (9.71 g) at room temperature under nitrogen. After stirring for 20 hours, the reaction mixture was filtered through a pad of celite and the solid DCU was washed with DCM. Concentration of the filtrate gave the crude product. Purification via flash column chromatography (silica gel, 30% ethyl acetate/hexane) afforded 8.50 g of the product as a solid, m.p. 153°-155° C.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of celite
  2. washthe solid DCU was washed with DCM
  3. customConcentration of the filtrate gave the crude product
  4. customPurification via flash column chromatography (silica gel, 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1435ff1b9a0347d887ce03f141849332
Source dataset
uspto-grants-1995_06
Patent number
US05428053

Linked notes

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