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Dicyclohexylcarbodiimide → (S)-Phenylmethyl-[1-(hydroxymethyl)-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate

HRID 22384
Notes
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Reaction equation

HRID 22384 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.[C:7]([NH:17][C@H:18]([C:21](O)=[O:22])[CH2:19][OH:20])([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C)C=O>[C:11]1([CH2:10][O:9][C:7](=[O:8])[NH:17][C@@H:18]([CH2:21][OH:22])[C:19](=[O:20])[NH:1][N:2]2[CH:6]=[CH:5][CH:4]=[CH:3]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 100310N-(Benzyloxycarbonyl)-L-serineHCID 1365891-Aminopyrrole

Product 1

HCID 10979597(S)-Phenylmethyl-[1-(hydroxymethyl)-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamateYield 61.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 1-aminopyrrole (3.28 g) and carbobenzyloxy-L-serine (9.57 g) in 100 ml of dry DCM and 10 ml of dry dimethylformamide was added DCC (10.0 g) at 0° C. After 10 minutes the ice bath was removed and the reaction mixture was stirred at room temperature overnight. The precipitate was filtered and stirred in boiling ethyl acetate. The mixture was filtered and the filtrate was combined with the filtrate of the reaction mixture and evaporated to dryness. The residue was purified by flash column chromatography (silica gel, DCM/methanol 20:1). The appropriate fractions were concentrated and the residue recrystallized from ethyl acetate to afford 7.48 g of the product as crystals, m.p. 163°-164° C.

Workup

  1. customAfter 10 minutes the ice bath was removed
  2. filtrationThe precipitate was filtered
  3. stirringstirred
  4. filtrationThe mixture was filtered
  5. customevaporated to dryness
  6. customThe residue was purified by flash column chromatography (silica gel, DCM/methanol 20:1)
  7. concentrationThe appropriate fractions were concentrated
  8. customthe residue recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5ac3fc4d12bd452fb2c705c10ffb9334
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05428053

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes