Acetic Anhydride → diphenylmethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetraacetoxy-5-(N-benzyloxycarbonyl-L-leucyl)aminohexanoyl]amino-3-phenylpropionate

HRID 2230411Notes

Reaction equation

HRID 2230411 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:54][OH:55])[C@@H:21]([OH:53])[C@@H:22]([OH:52])[C@H:23]([OH:51])[C:24]([NH:26][C@H:27]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:28][C:29]([O:31][CH:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])=[O:25])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[C:60](=[O:62])[CH3:61])(=O)C>N1C=CC=CC=1>[C:1]([O:51][C@@H:23]([C@H:22]([O:52][C:60](=[O:62])[CH3:61])[C@H:21]([O:53][C:24](=[O:25])[CH3:23])[C@@H:20]([NH:19][C:17](=[O:18])[C@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:54][O:55][C:17](=[O:18])[CH3:12])[C:24]([NH:26][C@H:27]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[CH2:28][C:29]([O:31][CH:32]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:30])=[O:25])(=[O:8])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 59902693diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate

Product 1

HCID 59902695diphenylmethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetraacetoxy-5-(N-benzyloxycarbonyl-L-leucyl)aminohexanoyl]amino-3-phenylpropionate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate (200 mg) in pyridine (5 ml) was added acetic anhydride (3 ml) and the mixture was stirred at room temperature for 4 days. After concentration under reduced pressure, the residue was dissolved in ethyl acetate (100 ml) and washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine respectively. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was passed through silica gel column chromatography, followed by elution with ethyl acetate-hexane (1:1). The effective fractions were combined and concentrated under reduced pressure to afford the title compound (85 mg).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  3. washwashed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine respectively
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washfollowed by elution with ethyl acetate-hexane (1:1)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-893a5ea6236a4c7a958bd984052f758e
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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