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Dicyclohexylcarbodiimide → 4-(2,5-Anhydro-4-bromo-3,4-dideoxy-D-erythropentonoyl)-1-piperazinecarboxylic acid phenylmethyl ester

HRID 54789
Notes
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Reaction equation

HRID 54789 reaction equation
[Br:1][C@@H:2]1[CH2:9][O:8][C@@H:4]([C:5]([OH:7])=O)[CH2:3]1.ON1C2C=CC=CC=2N=N1.[CH2:20]([O:27][C:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(N=C=NC2CCCCC2)CCCCC1>O.CN(C)C=O.C(Cl)Cl>[C:21]1([CH2:20][O:27][C:28]([N:30]2[CH2:35][CH2:34][N:33]([C:5]([C@@H:4]3[O:8][CH2:9][C@@H:2]([Br:1])[CH2:3]3)=[O:7])[CH2:32][CH2:31]2)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 643495Benzyl piperazine-1-carboxylateHCID 676487252,5-Anhydro-4-bromo-3,4-dideoxy-D-erythro-pentonic acid

Product 1

HCID 1317198554-(2,5-Anhydro-4-bromo-3,4-dideoxy-D-erythropentonoyl)-1-piperazinecarboxylic acid phenylmethyl esterYield 57.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.941 g of product from Example 150, 0.652 g of 1-hydroxybenzotriazole, 1.17 g of 1-benzyloxycarbonyl piperazine, 1.39 g of dicyclohexylcarbodiimide and 8 ml of dry methylene chloride is stirred at room temperature for 1 hour. Five ml of dimethylformamide is added and the stirring continued overnight at room temperature. The reaction mixture is diluted with water and extracted with chloroform. The organic layer is dried, concentrated in vacuo and the residue purified by chromatography (silica gel: 10-80% ethyl acetate/hexane) to give 1.1 g of the desired product.

Workup

  1. customthe stirring continued overnight
  2. customat room temperature
  3. extractionextracted with chloroform
  4. customThe organic layer is dried
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by chromatography (silica gel: 10-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d23b9cb991464243b285bc1e2e58ccff
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05623081

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes