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

HRID 1290400Notes

Reaction equation

HRID 1290400 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

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-ae5a4a8505ad40ef81afc892c0a4f54f
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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