Hydrochloric Acid → HCID 20592175, compound

HRID 1368868Notes

Reaction equation

HRID 1368868 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([P:14]([O:34]C)([O:16][C@@H:17]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:18]([O:20]C)=[O:19])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([P:14]([OH:34])([O:16][C@@H:17]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:18]([OH:20])=[O:19])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12074006HCID 12074006, compound

Product 1

HCID 20592175HCID 20592175, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A methanol (1 ml) solution of the methyl (S)-2-(((R)-1-(benzyloxycarbonylamino)ethyl)(methoxyphosphinoyl)oxy)-6-(tert-butoxycarbonylamino)hexanoate (9.7 mg) obtained in the above step (a)was added with potassium carbonate (5.7 mg), and the mixture was stirred at room temperature for 3 hours. The mixture was acidified with hydrochloric acid and the organic substances were extracted with ethyl acetate. The extract was washed with saturated brine, and then the organic layer was dried over anhydrous sodium sulfate to obtain (S)-2-(((R)-1-(benzyloxycarbonylamino)ethyl)(hydroxyphosphinoyl)oxy)-6-(tert-butoxycarbonylamino)hexanoic acid (3.1 mg, 34%). This compound was subjected to the measure m en t of molecular weight and then used in the following reaction without further purification.

Workup

  1. extractionthe organic substances were extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-1356406a4f3d46afa3776d946ab169ee
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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