Hydrochloric Acid → HCID 20592175, compound

HRID 1582584Notes

Reaction equation

HRID 1582584 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 measurement 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-b3a3f77609d849dcae865fad395c08fd
Source dataset
uspto-grants-2004_05
Patent number
US06737416B2

Reaction notes

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