Hydrochloric Acid → HCID 11662391, compound

HRID 1685540Notes

Reaction equation

HRID 1685540 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][C:6]1[N:7]=[C:8]([NH:12][C:13](=[O:31])[CH:14]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[CH2:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[S:9][C:10]=1[CH3:11])C.[OH-].[Na+].Cl>O1CCOCC1>[CH:16]1([CH2:15][CH:14]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[C:13]([NH:12][C:8]2[S:9][C:10]([CH3:11])=[C:6]([CH2:5][C:4]([OH:32])=[O:3])[N:7]=2)=[O:31])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11648626HCID 11648626, compound

Product 1

HCID 11662391HCID 11662391, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

{2-[3-Cyclopentyl-2-(4-methanesulfonylphenyl)-propionylamino]-5-methyl-thiazol-4-yl}-acetic acid ethyl ester (49 mg, 0.1 mmol), dioxan (0.5 mL), and 1 N sodium hydroxide were stirred at room temperature for 20 h. The pH was adjusted to approx. 3 with 1 N hydrochloric acid (0.5 mL), the reaction mixture was concentrated in vacuo, and the precipitate was isolated by filtration. Yellow crystals of the title compound were washed with water and dried to give 43 mg (yield: 93%). 1H-NMR (CDCl3): δ 7.85 (d, 2H), 7.58 (d, 2H), 3.78 (t, 1H), 3.62 (s, 2H), 3.01 (s, 3H), 2.42 (s, 3H), 2.22-2.15 (m, 1H), 1.93-1.86 (m, 1H), 1.75-1.49 (m, 7H), 1.15-1.02 (m, 2H); HPLC-MS: m/z=451 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe precipitate was isolated by filtration
  3. washYellow crystals of the title compound were washed with water
  4. customdried
  5. customto give 43 mg (yield: 93%)

Sources & evidence

ORD record
ord-4c7b5e4f5111484185821d7d48ac2a4d
Source dataset
uspto-grants-2012_04
Patent number
US08148412B2

Reaction notes

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