Hydrochloric Acid → HCID 70577286, compound

HRID 1427251Notes

Reaction equation

HRID 1427251 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)([CH2:13][CH3:14])[C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.[Li+].[OH-].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19]([NH:24][S:25]([CH3:28])(=[O:26])=[O:27])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)([CH2:13][CH3:14])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57524786HCID 57524786, compound

Product 1

HCID 70577286HCID 70577286, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 2-(4-chlorophenyl)-2-(4-(methylsulfonamido)-1H-indol-1-yl)butanoate (840 mg, 2 mmol), as described in Example 3 step C, and 2 M LiOH (5 mL) in methanol (5 mL) was heated to 50° C. for 5 h. The reaction was acidified with 1M HCl and the volatile was removed under reduced pressure. The residue was dissolved in ethyl acetate (80 mL) and water (20 mL). The organic layer was washed with brine (10 mL) and dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as colorless solid. LC/MS 407.0 (M+1).

Workup

  1. customthe volatile was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (80 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d75323cd4a14a89abb5f81a4bee408f
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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