Piperidine → HCID 11204538, compound

HRID 2230409Notes

Reaction equation

HRID 2230409 reaction equation
[C:1]([O:5][CH2:6][C@@H:7]([C:26]([NH:28][C@@H:29]([CH2:63][OH:64])[C@@H:30]([OH:62])[C@@H:31]([OH:61])[C@H:32]([OH:60])[C:33]([NH:35][C@H:36]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH2:37][C:38]([O:40][CH:41]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])=[O:34])=[O:27])[NH:8]C(OCC1C2CC3C(=CC=CC=3)C=2C=CC=1)=O)([CH3:4])([CH3:3])[CH3:2].N1CCCCC1>>[C:1]([O:5][CH2:6][C@@H:7]([C:26]([NH:28][C@@H:29]([CH2:63][OH:64])[C@@H:30]([OH:62])[C@@H:31]([OH:61])[C@H:32]([OH:60])[C:33]([NH:35][C@H:36]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH2:37][C:38]([O:40][CH:41]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:39])=[O:34])=[O:27])[NH2:8])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 8082PiperidineHCID 86758378HCID 86758378, compound

Product 1

HCID 11204538HCID 11204538, compoundYield 82.7%

Procedure

To diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-(O-tert-butyl-N-fluorenylmethyloxycarbonyl-L-seryl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate (874 mg) was added piperidine (5 ml) and the mixture was stirred at room temperature for 5 hours. Removal of the organic solvent gave a residue, which was subjected to flush silica gel column chromatography, followed by elution with methanol-ethyl acetate (1:2). The effective fractions were combined and concentrated under reduced pressure. The residue was recrystallized from diethylether-hexane to afford the title compound (539 mg).

Workup

  1. customRemoval of the organic solvent
  2. customgave a residue, which
  3. customto flush silica gel column chromatography
  4. washfollowed by elution with methanol-ethyl acetate (1:2)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from diethylether-hexane

Sources & evidence

ORD record
ord-c6c507e9430d45f49d176df17582d369
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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