Dimethylformamide → HCID 19991658, compound

HRID 1283840Notes

Reaction equation

HRID 1283840 reaction equation
C([N:11]1[CH2:18][CH2:17][CH2:16][CH:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.[CH2:19](O)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].CN(C)C=O.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[CH2:19]([O:15][C:13]([CH:12]1[CH2:16][CH2:17][CH2:18][NH:11]1)=[O:14])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81031-HexanolHCID 10868DicyclohexylcarbodiimideHCID 232388N-(Carbobenzyloxy)-DL-proline

Product 1

HCID 19991658HCID 19991658, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 24.9 g. (0.01 mol.) of N-carbobenzoxy-DL-proline and 11.22 g. (0.11 mol.) of n-hexanol in 200 ml. of dry dimethylformamide and 7.9 g. pyridine at room temperature is added 20.6 g. (0.01 mol.) of N,N'-dicyclohexylcarbodiimide. After stirring this mixture at room temperature for 16 hours, the precipitated N,N'-dicyclohexylurea is filtered off, the filtrate is diluted with a large volume of saturated aqueous sodium chloride, and this is thoroughly extracted with chloroform. The combined extracts are dried and concentrated in vacuo to give an oil comprising 1-(benzyloxy)carbonyl)]-2-[(hexyloxy)carbonyl]pyrrolidine.

Workup

  1. filtrationthe precipitated N,N'-dicyclohexylurea is filtered off
  2. additionthe filtrate is diluted with a large volume of saturated aqueous sodium chloride
  3. extractionthis is thoroughly extracted with chloroform
  4. customThe combined extracts are dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e996256af16447ef85c4566829499577
Source dataset
uspto-grants-1976_08
Patent number
US03976660

Reaction notes

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