HCID 10100590, compound → HCID 10054418, compound

HRID 1492770Notes

Reaction equation

HRID 1492770 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:11][N:12]3[C:16]([C:17]([O:19]CC)=[O:18])=[C:15]([Cl:22])[N:14]=[C:13]3[CH2:23][CH3:24])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][S:32]([C:35]([F:38])([F:37])[F:36])(=[O:34])=[O:33]>CO.[OH-].[Na+]>[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:11][N:12]3[C:16]([C:17]([OH:19])=[O:18])=[C:15]([Cl:22])[N:14]=[C:13]3[CH2:23][CH3:24])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][S:32]([C:35]([F:37])([F:38])[F:36])(=[O:34])=[O:33]

Participants

4

Reactant 1

HCID 10100590HCID 10100590, compound

Product 1

HCID 10054418HCID 10054418, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of product of Example 95 (0.4 g) in methanol (20 ml) and 2M NaOH (4 ml) was heated at reflux for 1.5 h. The solution was concentrated in vacuo. It was then diluted with water (10 ml) and extracted with diethyl ether (10 ml). The aqueous layer was acidified to pH5 with 2N HCl and extracted with ethyl acetate (3×20 ml). The combined organic extracts were dried and concentrated in vacuo to give the title compound (0.35 g) as a pale beige solid, m.p. 109°-110° (dec.).

Workup

  1. temperatureat reflux for 1.5 h
  2. concentrationThe solution was concentrated in vacuo
  3. additionIt was then diluted with water (10 ml)
  4. extractionextracted with diethyl ether (10 ml)
  5. extractionextracted with ethyl acetate (3×20 ml)
  6. customThe combined organic extracts were dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8bc59d0ea8314d61942f1f96d742fea9
Source dataset
uspto-grants-1994_12
Patent number
US05374646

Reaction notes

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