Triethylamine → HCID 131714446, compound

HRID 1583952Notes

Reaction equation

HRID 1583952 reaction equation
C(N(CC)CC)C.[C:8]([O:14][CH2:15]Cl)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[C:17]([NH:25][CH:26]([CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH2:27][P:28]([CH2:31][C:32]([N:34]1[CH2:48][CH2:47][CH2:46][C@H:35]1[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])=[O:33])([OH:30])=[O:29])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O.C(OCC)(=O)C>[C:17]([NH:25][CH:26]([CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH2:27][P:28]([CH2:31][C:32]([N:34]1[CH2:48][CH2:47][CH2:46][C@H:35]1[C:36]([O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])=[O:33])([O:30][CH2:15][O:14][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:29])(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 87885Chloromethyl pivalateHCID 131714447HCID 131714447, compound

Product 1

HCID 131714446HCID 131714446, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

An equimolar mixture of triethylamine and chloromethyl pivalate are added to a solution of (S)-1-[[[2-(benzoylamino)-3-phenylpropyl]hydroxyphosphinyl]acetyl]-L-proline, phenylmethyl ester, prepared, for example, as set forth in Example 1(g), 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 (S)-1-[[[2-(benzoylamino)-3-phenylpropyl][(2,2-dimethyl-1-oxopropoxy)methoxy]phosphinyl]acetyl]-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-8051b7597c464329aae69764a8373b74
Source dataset
uspto-grants-1985_11
Patent number
US04555506

Reaction notes

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