Potassium Hydroxide → HCID 121482660, compound

HRID 1483927Notes

Reaction equation

HRID 1483927 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]([SH:37])([C:33]([F:36])([F:35])[F:34])[CH2:11][C:12]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[C:19]2([CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23]2)[O:18][CH2:17]3)=[O:13])[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].[OH-].[K+].[NH2:40]OS(O)(=O)=O>O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:33]([F:34])([F:36])[F:35])[S:37][NH:40][C:12]([C:14]3[CH:15]=[C:16]4[CH2:17][O:18][C:19]5([CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])[CH2:23]5)[C:20]4=[CH:21][CH:22]=3)([OH:13])[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

6

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 76284hydroxylamine-O-sulfonic acidHCID 121482666HCID 121482666, compound

Product 1

HCID 121482660HCID 121482660, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 6 (530 mg) in a solution of potassium hydroxide (182 mg) in water (9 mL) was added a solution of hydroxylamine-O-sulfonic acid (183 mg, 2 eq) in a solution of potassium hydroxide (273 mg) in water (18 mL) and the resulting mixture was stirred at room temperature for 30 min under nitrogen. The mixture was diluted with ethyl acetate and washed with brine. The organic extract was concentrated and subjected to silica gel column chromatography (0 to 30% ethyl acetate in heptane) to yield 150 mg of Intermediate 7 as a mixture of diastereomers.

Workup

  1. washwashed with brine
  2. extractionThe organic extract
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-847b9678ba854e448774c0e791439c10
Source dataset
uspto-grants-2016_08
Patent number
US09420793B2

Reaction notes

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