Trifluoroacetic acid → HCID 178510572, compound

HRID 928118Notes

Reaction equation

HRID 928118 reaction equation
[NH2:1][CH:2]([C:14]1[S:15][C:16]([Br:19])=[CH:17][N:18]=1)[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11]CC)=[O:10])[CH2:5][CH2:4]1.[OH-].[Na+].C(O)(C(F)(F)F)=O>CO>[NH2:1][CH:2]([C:14]1[S:15][C:16]([Br:19])=[CH:17][N:18]=1)[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 178472362HCID 178472362, compound

Product 1

HCID 178510572HCID 178510572, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

The crude mixture from Step 1 was dissolved in methanol (3 mL), and sodium hydroxide (1.0 M in water, 0.950 mL, 0.950 mmol) was added to the resulting solution. The reaction mixture was then heated to a temperature of 50° C. for 30 minutes. The reaction was subsequently cooled, acidified with TFA (0.1 mL) and concentrated to afford racemic trans-4-[amino(5-bromo-1,3-thiazol-2-yl)methyl]cyclohexanecarboxylic acid, which was used in subsequent synthetic transformations without purification. MS ESI calc'd. for C11H15BrN2O2S [M+H]+ 319, 321. found 319, 321.

Workup

  1. temperatureThe reaction was subsequently cooled
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-de07c11461d24bd88bfb58d9db13e6f4
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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