Hydrochloric Acid → HCID 90016025, compound

HRID 920151Notes

Reaction equation

HRID 920151 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:32])=[C:6]([C@:8]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[O:30][CH3:31])([CH3:19])[CH2:9][S:10][C:11]([CH3:18])([CH3:17])[C:12]([O:14]CC)=[O:13])[CH:7]=1.[OH-].[Na+].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:32])=[C:6]([C@:8]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[O:30][CH3:31])([CH3:19])[CH2:9][S:10][C:11]([CH3:18])([CH3:17])[C:12]([OH:14])=[O:13])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90067143HCID 90067143, compound

Product 1

HCID 90016025HCID 90016025, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (R)-ethyl 2-(2-(5-bromo-2-fluorophenyl)-2-(2,4-dimethoxybenzylamino) propylthio)-2-methylpropanoate (3 g, 5.68 mmol, Eq: 1.00) in ethanol (35.7 ml) was added 3 N NaOH (3.78 ml, 11.4 mmol, Eq: 2.0). The reaction mixture was stirred at 70° C. for 2 hours. 1 N HCl (11.4 ml, 11.4 mmol, Eq: 2.0) was added to the reaction mixture at 23° C. (pH=5-6) and evaporated. The residue was triturated with dichloromethane/methanol 9:1, solid Na2SO4 was added. The mixture was filtered off. The filtrate was evaporated to dryness to give the crude (R)-2-(2-(5-bromo-2-fluorophenyl)-2-(2,4-dimethoxybenzylamino)propylthio)-2-methylpropanoic acid (2.6 g, 5.2 mmol, 91.5% yield) as an off-white foam which was used without further purification. MS (ISP): m/z=500.0 [M+H]+ and 502.3 [M+2+H]+.

Workup

  1. customevaporated
  2. customThe residue was triturated with dichloromethane/methanol 9:1, solid Na2SO4
  3. additionwas added
  4. filtrationThe mixture was filtered off
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-7ae4f58cfb924a6eb3ba51099921b05f
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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