Triethylamine → HCID 131713508, compound

HRID 544101Notes

Reaction equation

HRID 544101 reaction equation
C(N(CC)CC)C.[C:8]([O:14][CH2:15]Cl)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[CH2:17]([N:19]([CH2:37][P:38]([OH:50])([CH2:40][CH2:41][CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:39])[C:20]([N:22]1[CH2:36][CH2:35][CH2:34][C@H:23]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:21])[CH3:18]>CN(C)C=O.C(OCC)(=O)C>[CH2:17]([N:19]([CH2:37][P:38]([O:50][CH2:15][O:14][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])([CH2:40][CH2:41][CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:39])[C:20]([N:22]1[CH2:36][CH2:35][CH2:34][C@H:23]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:21])[CH3:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 87885Chloromethyl pivalateHCID 131713509HCID 131713509, compound

Product 1

HCID 131713508HCID 131713508, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

An equimolar mixture of triethylamine and chloromethyl pivalate are added to a solution of 1-[[ethyl[[hydroxy(4-phenylbutyl)phosphinyl]methyl]amino]carbonyl]-L-proline, phenylmethyl ester in dimethylformamide under argon. The mixture is stirred for several hours at room temperature, diluted with ethyl acetate, washed with water, brine, dried (MgSO4), and evaporated. The crude product is chromatographed to give 1-[[ethyl[[[(2,2-dimethyl-1-oxopropoxy) methoxy](4-phenylbutyl)phosphinyl]methyl]amino]carbonyl]-L-proline, phenylmethyl ester.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe crude product is chromatographed

Sources & evidence

ORD record
ord-1350c95ec77c4a1996be301f5802cb67
Source dataset
uspto-grants-1984_05
Patent number
US04448772

Reaction notes

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