Hydrochloric Acid → HCID 178467399, compound

HRID 928132Notes

Reaction equation

HRID 928132 reaction equation
[OH-].[Na+].[Br:3][C:4]1[S:8][C:7]([C:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([O:20]CCCC)=[O:19])[CH2:14][CH2:13]2)([OH:11])[CH3:10])=[N:6][CH:5]=1.Cl.O>CO>[Br:3][C:4]1[S:8][C:7]([C:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]2)([OH:11])[CH3:10])=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178451147HCID 178451147, compound

Product 1

HCID 178467399HCID 178467399, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Sodium hydroxide (3.0 M in H2O, 5.98 mL, 17.93 mmol) was added to a solution of racemic butyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-1-hydroxyethyl]cyclohexanecarboxylate (2.0 g, 5.12 mmol) in methanol (6 mL) and heated to 70° C. for 3 hour. Then, the reaction was cooled to room temperature and acidified with hydrochloric acid (3.0 M in H2O). Water (10 mL) was added and the mixture was stirred overnight at which point crystallization occurred. The reaction was filtered and the filter cake was washed with water and then dried under a nitrogen bag to afford racemic trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-1-hydroxyethyl]cyclohexanecarboxylic acid as a white solid. MS ESI calc'd. for C12H17BrNO3S [M+H]+ 334, 336. found 334, 336. 1H NMR (600 MHz, DMSO-d6) δ 11.92 (s, 1H), 7.69 (s, 1H), 5.91 (s, 1H), 2.03-1.93 (m, 1H), 1.92-1.85 (m, 1H), 1.85-1.77 (m, 2H), 1.62-1.51 (m, 1H), 1.48-1.35 (m, 4H), 1.25-1.08 (m, 3H), 1.04-0.88 (m, 1H).

Workup

  1. temperatureThen, the reaction was cooled to room temperature
  2. filtrationThe reaction was filtered
  3. washthe filter cake was washed with water
  4. customdried under a nitrogen bag

Sources & evidence

ORD record
ord-41c31315347b43ff9caf0a59fb7e08e2
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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