Dicyclohexylcarbodiimide → HCID 13457743, compound

HRID 280122Notes

Reaction equation

HRID 280122 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[NH2:16][N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:30]([NH:40][CH2:41][C:42](O)=[O:43])([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>ClCCl>[C:30]([NH:40][CH2:41][C:42]([NH:16][N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22](=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:43])([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 13457732HCID 13457732, compound

Product 1

HCID 13457743HCID 13457743, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N'-Dicyclohexylcarbodiimide (2.32 g, 11.2 mmol) was added in one portion to a stirred solution of 1-amino-2-benzoylpyrrole (2.1 g, 11.2 mmol) and carbobenzyloxyglycine (2.36 g, 11.2 mmol) in 70 ml of dichloromethane. The reaction mixture was stirred rapidly for 2.5 hours at room temperature and thereafter filtered to remove the precipitated dicyclohexylurea. Evaporation of the filtrate left 4.7 g of a semi-solid which was flash chromatographed (silica gel, 1:1 ethyl acetate-hexane) to give 3.75 g (88%) of powder, m.p. 96°-98°.

Workup

  1. filtrationfiltered
  2. customto remove the precipitated dicyclohexylurea
  3. customEvaporation of the filtrate
  4. waitleft 4.7 g of a semi-solid which
  5. customchromatographed (silica gel, 1:1 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-9c718551f8954ad7be22d7812c888411
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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