Triethylamine → HCID 131712760, compound

HRID 851435Notes

Reaction equation

HRID 851435 reaction equation
C(N(CC)CC)C.[C:8]([O:14][CH2:15]Cl)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[OH:17][P:18]([CH2:30][C:31]([N:33]1[CH2:47][CH2:46][CH2:45][C@H:34]1[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])=[O:32])([CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:19]>CN(C)C=O.C(OCC)(=O)C>[CH3:10][C:9]([CH3:12])([CH3:11])[C:8](=[O:13])[O:14][CH2:15][O:19][P:18]([CH2:30][C:31]([N:33]1[CH2:47][CH2:46][CH2:45][C@H:34]1[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])=[O:32])([CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 87885Chloromethyl pivalateHCID 131712761HCID 131712761, compound

Product 1

HCID 131712760HCID 131712760, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (1.9 ml) and chloromethyl pivalate (2.0 ml) are added to a solution of 3.0 g of [[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline, benzyl ester in dimethylformamide under an argon atmosphere and the resulting mixture is stirred at room temperature for 6 hours. The reaction mixture is diluted with ethyl acetate, washed with water, brine, dried (MgSO4), and evaporated. The crude product (3.7 g) is chromatographed on silica (80 g) eluting with ethyl acetate/dichloromethane to give 2.96 g of the title compound.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe crude product (3.7 g) is chromatographed on silica (80 g)
  5. washeluting with ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-f8bafaf4f5304f0fa33ea8cca6cd70b6
Source dataset
uspto-grants-1983_05
Patent number
US04384123

Reaction notes

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