Hydrochloric Acid → HCID 59902678, compound

HRID 2230410Notes

Reaction equation

HRID 2230410 reaction equation
C([O:5][CH2:6][C@@H:7]([C:9]([NH:11][C@@H:12]([CH2:46][OH:47])[C@@H:13]([OH:45])[C@@H:14]([OH:44])[C@H:15]([OH:43])[C:16]([NH:18][C@H:19]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:20][C:21]([O:23]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:22])=[O:17])=[O:10])[NH2:8])(C)(C)C.Cl>C(OCC)(=O)C>[OH:43][C@@H:15]([C@H:14]([OH:44])[C@H:13]([OH:45])[C@@H:12]([NH:11][C:9](=[O:10])[C@H:7]([CH2:6][OH:5])[NH2:8])[CH2:46][OH:47])[C:16]([NH:18][C@H:19]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:20][C:21]([OH:23])=[O:22])=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11204538HCID 11204538, compound

Product 1

HCID 59902678HCID 59902678, compoundYield 105.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-(O-tert-butyl-L-seryl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate (300 mg) was added 4N hydrogen chloride solution in ethyl acetate (10 ml) and the mixture was stirred at room temperature for 1.5 hours. Removal of the organic solvent gave a residue, which was extracted with water. The aqueous layer was washed with diethylether and concentrated under reduced pressure. The residue was recrystallized from methanol-diethylether to afford the title compound (208 mg).

Workup

  1. customRemoval of the organic solvent
  2. customgave a residue, which
  3. extractionwas extracted with water
  4. washThe aqueous layer was washed with diethylether
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from methanol-diethylether

Sources & evidence

ORD record
ord-346821a57c644186963907dd6aee1c9c
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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