Water → diphenylmethyl (S)-3-[(2S,3R,4R,55)-2,3,4,6-tetrahydroxy-5-((N,N-dimethyl-L-valyl)-L-leucyl)aminohexanoyl]amino-3-phenylpropionate

HRID 2230417Notes

Reaction equation

HRID 2230417 reaction equation
[CH3:1][N:2]([CH3:10])[C@H:3]([C:7](O)=[O:8])[CH:4]([CH3:6])[CH3:5].[OH:11][C@@H:12]([C@H:40]([OH:55])[C@H:41]([OH:54])[C@@H:42]([NH:45][C:46](=[O:53])[C@H:47]([CH2:49][CH:50]([CH3:52])[CH3:51])[NH2:48])[CH2:43][OH:44])[C:13]([NH:15][C@H:16]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:17][C:18]([O:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[O:14].C(N(CC)CC)C.O>CN(C)C=O>[OH:11][C@@H:12]([C@H:40]([OH:55])[C@H:41]([OH:54])[C@@H:42]([NH:45][C:46](=[O:53])[C@H:47]([CH2:49][CH:50]([CH3:51])[CH3:52])[NH:48][C:7](=[O:8])[C@H:3]([CH:4]([CH3:6])[CH3:5])[N:2]([CH3:10])[CH3:1])[CH2:43][OH:44])[C:13]([NH:15][C@H:16]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:17][C:18]([O:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11008044N,N-Dimethyl-L-ValineHCID 11039599diphenylmethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate

Product 1

HCID 59902701diphenylmethyl (S)-3-[(2S,3R,4R,55)-2,3,4,6-tetrahydroxy-5-((N,N-dimethyl-L-valyl)-L-leucyl)aminohexanoyl]amino-3-phenylpropionateYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N,N-dimethyl-L-valine (58 mg) and diphenylmethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionate (250 mg) in dimethylformamide (4 ml) were added diethyl cyanophosophonate (82 mg) and triethylamine (0.14 ml) and the mixture was stirred at room temperature for 18 hours. After addition of water, the whole was extracted with ethyl acetate and the extract was washed with saturated brine, followed by drying over anhydrous sodium sulfate. Removal of the organic solvent gave a residue, which was recrystallized from ehtyl acetate-hexane to afford the title compound (282 mg).

Workup

  1. extractionthe whole was extracted with ethyl acetate
  2. washthe extract was washed with saturated brine
  3. dry with materialby drying over anhydrous sodium sulfate
  4. customRemoval of the organic solvent
  5. customgave a residue, which
  6. customwas recrystallized from ehtyl acetate-hexane

Sources & evidence

ORD record
ord-1303f71bf31748919d12826580d2042a
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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