Water → HCID 54208557, compound

HRID 1728770Notes

Reaction equation

HRID 1728770 reaction equation
[C:1]([NH:4][CH:5]([C:16](=[O:33])[CH:17]=[CH:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=1)[CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O>C(O)C.ClCCl>[C:1]([NH:4][CH:5]([CH:16]([OH:33])[CH:17]=[CH:18][C:19]1[CH:24]=[C:23]([C:25]([F:27])([F:28])[F:26])[CH:22]=[C:21]([C:29]([F:30])([F:31])[F:32])[CH:20]=1)[CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 53694173HCID 53694173, compound

Product 1

HCID 54208557HCID 54208557, compound

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

A solution of the product of Example 1 (2.0 g) was dissolved in ethanol/dichloromethane (5:1, 100 ml) and treated with sodium borohydride (0.156 g). The reaction was stirred for 1 hour and then poured into water (500 ml), extracted with ethyl acetate, dried (MgSO4), filtered, and evaporated to yield an oil which was purified by chromatography on silica using ethyl acetate/petroleum ether (bp 60°-80° C.) to yield the title compound isomer A as a pale yellow solid (0.25 g) mp=190°-191° C.; found: C, 56.19; H, 3.93; N, 2.91; C23H19F6NO2S.0.25H2O requires C, 56.15; H, 4.00; N, 2.85%.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto yield an oil which
  6. customwas purified by chromatography on silica

Sources & evidence

ORD record
ord-1ca09c46329647b38a7e024f72c987f6
Source dataset
uspto-grants-1994_07
Patent number
US05328927

Reaction notes

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