Acetic Anhydride → HCID 86758379, compound

HRID 2230416Notes

Reaction equation

HRID 2230416 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([NH:18][C@H:19]([C:24]([NH:26][C@@H:27]([CH2:61][OH:62])[C@@H:28]([OH:60])[C@@H:29]([OH:59])[C@H:30]([OH:58])[C:31]([NH:33][C@H:34]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:35][C:36]([O:38][CH:39]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])=[O:32])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:63](OC(=O)C)(=[O:65])[CH3:64]>N1C=CC=CC=1>[C:63]([O:62][CH2:61][C@H:27]([NH:26][C:24](=[O:25])[C@H:19]([CH2:20][CH:21]([CH3:23])[CH3:22])[NH:18][C:16](=[O:17])[C@H:12]([CH:13]([CH3:15])[CH3:14])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C@@H:28]([OH:60])[C@@H:29]([OH:59])[C@H:30]([OH:58])[C:31]([NH:33][C@H:34]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:35][C:36]([O:38][CH:39]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])=[O:32])(=[O:65])[CH3:64]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 59902692HCID 59902692, compound

Product 1

HCID 86758379HCID 86758379, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-((N-benzyloxycarbonyl-L-valyl)-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate (200 mg) in pyridine (1 ml) was added acetic anhydride (0.0243 ml) and the mixture was stirred at room temperature for 14 hours. After concentration under reduced pressure, the residue was passed through silica gel column chromatography, followed by elution with ethyl acetate-methanol (20:1). The effective fractions were combined and concentrated under reduced pressure to give a residue, which was recrystallized from mthanol-diethylether to provide the title compound (103 mg).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. washfollowed by elution with ethyl acetate-methanol (20:1)
  3. concentrationconcentrated under reduced pressure
  4. customto give a residue, which
  5. customwas recrystallized from mthanol-diethylether

Sources & evidence

ORD record
ord-14cf6fd5a78342889ad351cd2116def3
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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