Hydrochloric Acid → HCID 53912131, compound

HRID 2230413Notes

Reaction equation

HRID 2230413 reaction equation
C(OC([NH:8][C@H:9]([C:22]([NH:24][C@@H:25]([CH2:59][OH:60])[C@@H:26]([OH:58])[C@@H:27]([OH:57])[C@H:28]([OH:56])[C:29]([NH:31][C@H:32]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH2:33][C:34]([O:36]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:35])=[O:30])=[O:23])[CH2:10][CH2:11][O:12]CC1C=CC(OC)=CC=1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[NH2:8][C@H:9]([C:22]([NH:24][C@@H:25]([CH2:59][OH:60])[C@@H:26]([OH:58])[C@@H:27]([OH:57])[C@H:28]([OH:56])[C:29]([NH:31][C@H:32]([C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)[CH2:33][C:34]([OH:36])=[O:35])=[O:30])=[O:23])[CH2:10][CH2:11][OH:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59902698HCID 59902698, compound

Product 1

HCID 53912131HCID 53912131, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-(N-tert-butoxycarbonyl-O-(4-methoxybenzyl)-L-homoseryl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate (200 mg) was added 4N hydrogen chloride in ethyl acetate (10 ml) at room temperature and the mixture was stirred at room temperature for 3 hours. After concentration under reduced pressure, the residue was dissolved in water and washed with diethylether. The aqueous layer was passed through a column of DIAION CHP-20P (Mitsubishi kasei corporation), followed by elution with water-acetonitrile. The effective fractions were combined and concentrated under reduced pressure. The residue was recrystallized from methanol-diethylether to afford the title compound (53 mg).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. washwashed with diethylether
  4. washfollowed by elution with water-acetonitrile
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from methanol-diethylether

Sources & evidence

ORD record
ord-db70d25c20db43c6afe2b01334d93949
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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