Hydrochloric Acid → HCID 57890189, compound

HRID 1819931Notes

Reaction equation

HRID 1819931 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][NH:5][C:6]([C:8]1[S:9][C:10]([C:14]([CH2:32][CH3:33])([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([CH2:29][CH3:30])([OH:28])[CH2:26][CH3:27])=[C:19]([CH3:31])[CH:18]=2)[CH2:15][CH3:16])=[CH:11][C:12]=1[CH3:13])=[O:7].[OH-].[Na+].Cl>CO.O>[CH2:15]([C:14]([C:10]1[S:9][C:8]([C:6]([NH:5][CH2:4][C:3]([OH:34])=[O:2])=[O:7])=[C:12]([CH3:13])[CH:11]=1)([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([CH2:26][CH3:27])([OH:28])[CH2:29][CH3:30])=[C:19]([CH3:31])[CH:18]=1)[CH2:32][CH3:33])[CH3:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10323260HCID 10323260, compound

Product 1

HCID 57890189HCID 57890189, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

2-[(5-{1-Ethyl-1-[4-(2-ethyl-2-hydroxy-butoxy)-3-methyl-phenyl]-propyl}-3-methyl-thiophene-2-carbonyl)-amino]-acetic acid methyl ester (Example 52) (0.34 g, 0.69 mmol) is dissolved in MeOH (2 mL), treated with H2O (0.5 mL) and NaOH (0.14 g, 3.47 mmol) and the resulting mixture is heated at a reflux for two hours cooled to at ambient temperature and stirred overnight. The solution is diluted with H2O (10 mL), the pH value is adjusted to about 3-4 using 1 M HCl, it is extracted with EtOAc (40 mL). The EtOAc layer is washed with brine (20 mL), dried with MgSO4, filtered and concentrated to yield the titled compound (0.244 g, 0.51 mmol, 74%). 1H NMR (CD3OD), δ 0.72 (t, J=7.4 Hz, 6H), 0.94 (t, J=7.4 Hz, 6H), 1.64-1.74 (m, 4H), 2.03-2.20 (m, 4H), 2.18 (s, 3H), 2.44 (s, 3H), 3.79 (s, 2H), 3.97-3.99 (m, 2H), 6.71 (s, 1H), 6.79 (d, J=8.2 Hz, 1H), 6.99-7.02 (m, 1H), 7.06-7.10 (m, 1H), 7.88-7.94 (t, J=5.7 Hz, 1H). LC/MS (m/z): calcd. for C26H36NO5S (M−H)−: 475.6; found: 474.3

Workup

  1. temperaturethe resulting mixture is heated at
  2. temperaturea reflux for two hours
  3. extractionis extracted with EtOAc (40 mL)
  4. washThe EtOAc layer is washed with brine (20 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-121834bd42b54b78b6eaa83cf7633d49
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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