Acetic Acid → 3-(Hydroxymethyl)-5-(pentafluoro-lambda6-sulphanyl)benzoic acid
Reaction equation
Cl.OC1CNC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[CH:25]([C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([S:36]([F:41])([F:40])([F:39])([F:38])[F:37])[CH:35]=1)[C:30]([OH:32])=[O:31])=[O:26]>ClCCl.O>[OH:26][CH2:25][C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([S:36]([F:41])([F:37])([F:38])([F:39])[F:40])[CH:35]=1)[C:30]([OH:32])=[O:31]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
54 mg (0.49 mmol) of 3-hydroxyazetidine hydrochloride, 97 mg (0.46 mmol) of sodium triacetoxyborohydride and 0.13 ml (2.35 mmol) of acetic acid were added in succession to a solution of 90 mg (0.32 mmol) of the compound of Example 36A in 3.2 ml of dichloromethane, and the mixture was stirred at RT for 1 h. A little water was then added, and the mixture was concentrated on a rotary evaporator. The residue was purified by preparative HPLC (Method 18). Evaporation of the appropriate fractions and drying of the residue under high vacuum gave 60 mg (66% of theory) of the title compound as the product of the reaction.
Workup
- concentrationthe mixture was concentrated on a rotary evaporator
- customThe residue was purified by preparative HPLC (Method 18)
- customEvaporation of the appropriate fractions
- customdrying of the residue under high vacuum
Sources & evidence
- ORD record
- ord-6ee1cc95b3a94ddcad5dc234a6021a83
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394309B2
Reaction notes
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