Water → HCID 58303811, compound

HRID 1886982Notes

Reaction equation

HRID 1886982 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[C:10]=1[S:18][C@@H:19]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C@@H:20]([OH:25])[C:21]([O:23][CH3:24])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl.O.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[NH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]=1[S:18][C@@H:19]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C@@H:20]([OH:25])[C:21]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 58303829HCID 58303829, compound

Product 1

HCID 58303811HCID 58303811, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
22 °C

Procedure

To 3.91 g (8.34 mmol) of (+/−)-(2S,3S)-methyl 3-(2-(benzyloxy)-6-nitrophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propanoate in 45 mL of ethyl acetate was added 11.3 g (5.00 mmol) of tin(II) chloride dihydrate, and the solution was stirred at 22° C. for 3.5 hours. Water, NaHCO3, and ethyl acetate were added, and the mixture was stirred at 22° C. for 1.5 hours. The stirring was stopped, and the mixture left to stand for 16 hours. The organic layer was partially separated from the aqueous layer, and the remaining mixture was filtered through Celite. The filtrate was extracted with ethyl acetate. The organic layers were combined, dried (Na2SO4), filtered, and evaporated to give (+/−)-(2S,3S)-methyl 3-(2-amino-6-(benzyloxy)phenylthio)-2-hydroxy-3-(4-methoxyphenyl)propanoate, which was used directly in the next step without purification.

Workup

  1. stirringthe mixture was stirred at 22° C. for 1.5 hours
  2. waitthe mixture left
  3. waitto stand for 16 hours
  4. customThe organic layer was partially separated from the aqueous layer
  5. filtrationthe remaining mixture was filtered through Celite
  6. extractionThe filtrate was extracted with ethyl acetate
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-1350e0b67ba24d68b889cecc6cb09c5b
Source dataset
uspto-grants-2013_08
Patent number
US08501727B2

Reaction notes

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