Methanol → HCID 57345254, compound

HRID 1259026Notes

Reaction equation

HRID 1259026 reaction equation
OS(O)(=O)=O.[C:6]([NH:9][C@@H:10]([CH2:14][S:15][C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])=[CH:21][C:20]=1[C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])=[O:17])[C:11]([OH:13])=[O:12])(=[O:8])[CH3:7].O.[CH3:44]O>>[C:6]([NH:9][C@H:10]([C:11]([O:13][CH3:44])=[O:12])[CH2:14][S:15][C:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])=[CH:21][C:20]=1[C:33]([O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:34])=[O:17])(=[O:8])[CH3:7]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 57345036HCID 57345036, compound

Product 1

HCID 57345254HCID 57345254, compoundYield 82%

Procedure

H2SO4 (0.020 mL, 0.343 mmol) was added to a solution of (R)-2-acetamido-3-((2′,4′-difluoro-3-(benzyloxycarbonyl)biphenyl-4-yloxy)carbonylthio)propanoic acid (54 mg, 0.102 mmol) in MeOH (10 mL). The reaction mixture was stirred at r.t. for 18 h, poured into H2O (30 mL) and extracted with CH2Cl2 (20 mL). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was purified by flash chromatography on SiO2 (3% MeOH/CH2Cl2) to furnish (R)-benzyl 4-((2-acetamido-3-methoxy-3-oxopropylthio)carbonyloxy)-2′,4′-difluorobiphenyl-3-carboxylate (yellow-coloured solid, yield: 82%).

Workup

  1. extractionextracted with CH2Cl2 (20 mL)
  2. dry with materialThe organic layer was dried over Na2SO4 (anhydrous)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography on SiO2 (3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7772461b87464b21b0aa7dbfe961259c
Source dataset
uspto-grants-2013_06
Patent number
US08466197B2

Reaction notes

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