HCID 57114159, compound → HCID 59902680, compound

HRID 2230397Notes

Reaction equation

HRID 2230397 reaction equation
[C:1]([O:4][C@@H:5]([C@H:22]([O:53][C:54](=[O:56])[CH3:55])[C@H:23]([O:49][C:50](=[O:52])[CH3:51])[C@@H:24]([NH:30][C:31](=[O:48])[C@H:32]([CH2:44][CH:45]([CH3:47])[CH3:46])[NH:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])[CH2:25][O:26][C:27](=[O:29])[CH3:28])[C:6]([O:8]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7])(=[O:3])[CH3:2]>FC(F)(F)C(O)=O>[C:1]([O:4][C@@H:5]([C@H:22]([O:53][C:54](=[O:56])[CH3:55])[C@H:23]([O:49][C:50](=[O:52])[CH3:51])[C@@H:24]([NH:30][C:31](=[O:48])[C@H:32]([CH2:44][CH:45]([CH3:47])[CH3:46])[NH:33][C:34]([O:36][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:35])[CH2:25][O:26][C:27](=[O:29])[CH3:28])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 57114159HCID 57114159, compound

Product 1

HCID 59902680HCID 59902680, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Diphenylmethyl (2S,3R,4R,5S)-2,3,4,6-tetraacetoxy-5-(N-benzyloxycarbonyl-L-leucyl)aminohexanoate (270 mg) was dissolved in trifluoroacetic acid (5 ml) and the solution was stirred at room temperature for 1 hour. After concentration under reduced pressure, the residue was passed through silica gel column chromatography, followed by elution with ethyl acetate-methanol (10:1). The effective fractions were combined and concent rated under reduced pressure to afford the title compound (214 mg).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. washfollowed by elution with ethyl acetate-methanol (10:1)

Sources & evidence

ORD record
ord-dba6acecb6214dbf8295927ba7185b9d
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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