Water → HCID 86654320, compound

HRID 1886983Notes

Reaction equation

HRID 1886983 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]=1[S:16][C@@H:17]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[C@@H:18]([OH:23])[C:19]([O:21]C)=[O:20].C(=O)(O)[O-].[Na+].O>CO.O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:3]=1[S:16][C@@H:17]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[C@@H:18]([OH:23])[C:19]([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 58303811HCID 58303811, compound

Product 1

HCID 86654320HCID 86654320, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
22 °C

Procedure

To a solution of 2.95 g (6.71 mmol) of (+/−)-(2S,3S)-methyl 3-(2-amino-6-(benzyloxy)phenylthio)-2-hydroxy-3-(4-methoxyphenyl)propanoate in 34 mL of 9:1 methanol/water was added 5.64 g (67.1 mmol) of sodium bicarbonate. The mixture was refluxed for 16 hours, cooled to 22° C., and 500 mL of water was added. The aqueous layer was washed with ethyl acetate (2×) and then acidified to ph 4-5 with conc. HCl. The mixture was extracted 3 times with a 7:3 ethyl acetate/methanol solution. The organic layers were combined, dried (Na2SO4), and evaporated to give (+/−)-(2S,3S)-3-(2-amino-6-(benzyloxy)phenylthio)-2-hydroxy-3-(4-methoxyphenyl)propanoic acid.

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. washThe aqueous layer was washed with ethyl acetate (2×)
  3. extractionThe mixture was extracted 3 times with a 7:3 ethyl acetate/methanol solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d77b890888e1404b85ce2b89a11fb12e
Source dataset
uspto-grants-2013_08
Patent number
US08501727B2

Reaction notes

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