Methanol → HCID 86666600, compound

HRID 1259028Notes

Reaction equation

HRID 1259028 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][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)=[O:34])=[O:17])[C:11]([OH:13])=[O:12])(=[O:8])[CH3:7].O.[CH3:46]O>>[C:6]([NH:9][C@H:10]([C:11]([O:13][CH3:46])=[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][C:40]([O:43][CH3:44])=[CH:41][CH:42]=1)=[O:34])=[O:17])(=[O:8])[CH3:7]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 71516599HCID 71516599, compound

Product 1

HCID 86666600HCID 86666600, compoundYield 30%

Procedure

H2SO4 (0.04 mL, 0.750 mmol) was added to a solution of (R)-2-acetamido-3-((2′,4′-difluoro-3-((4-methoxybenzyloxy)carbonyl)biphenyl-4-yloxy)carbonylthio)propanoic acid (160 mg, 0.286 mmol) in MeOH (25 mL). The reaction mixture was stirred at r.t. for 2 days, poured into H2O (100 mL) and extracted with CH2Cl2 (100 mL). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was purified by flash chromatography on SiO2 (5→80% EtOAc/hexanes) to furnish (R)-4-methoxybenzyl 4-((2-acetamido-3-methoxy-3-oxopropylthio)carbonyloxy)-2′,4′-difluorobiphenyl-3-carboxylate (white solid, yield: 30%).

Workup

  1. extractionextracted with CH2Cl2 (100 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 (5→80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1790a1cef3cd4d5d9bd7a21bf03f533d
Source dataset
uspto-grants-2013_06
Patent number
US08466197B2

Reaction notes

Loading…