Acetonitrile → HCID 21093936, compound

HRID 1350313Notes

Reaction equation

HRID 1350313 reaction equation
CC#N.O[Li].O.[CH3:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH2:31][CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[C:18]([NH:20][C:21]2[S:22][C:23]([C:26]([O:28]CC)=[O:27])=[CH:24][N:25]=2)=[O:19])=[CH:13][CH:12]=1)(=[O:10])=[O:9]>C1COCC1.O>[CH3:7][S:8]([C:11]1[CH:12]=[CH:13][C:14]([CH:17]([CH2:31][CH:32]2[CH2:33][CH2:34][O:35][CH2:36][CH2:37]2)[C:18]([NH:20][C:21]2[S:22][C:23]([C:26]([OH:28])=[O:27])=[CH:24][N:25]=2)=[O:19])=[CH:15][CH:16]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 168937Lithium hydroxide, monohydrateHCID 21094164HCID 21094164, compound

Product 1

HCID 21093936HCID 21093936, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
20 °C

Procedure

Ethyl 2-aminothiazole-5-carboxylate (2.21 g, 12.8 mmol) was condensed with 2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionic acid (Preparation 41, 1.00 g, 3.2 mmol), using the procedure described for EXAMPLE 65, to give ethyl 2-[2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionylamino]thiazole-5-carboxylate: m/z (ES+)=508.3 [M+MeCN+H]+. LiOH.H2O (410 mg, 9.8 mmol) was added to a solution of this ester (1.44 g, 3.1 mmol) in THF—H2O (3:1, 30 mL). The mixture was stirred at 20° C. for 16 h and then at 55° C. for 24 h. The solvents were removed in vacuo, then the residue was dissolved in H2O (50 mL). The aqueous solution was washed with EtOAc (20 mL), before being acidified to pH 1 with 2M HCl and extracted with EtOAc (2×100 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated to give a solid that was recrystallised (EtOAc-MeOH) to give the title compound: RTA=2.95 min; m/z (ES+)=480.2 [M+MeCN+H]+.

Workup

  1. waitat 55° C. for 24 h
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residue was dissolved in H2O (50 mL)
  4. washThe aqueous solution was washed with EtOAc (20 mL)
  5. extractionextracted with EtOAc (2×100 mL)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a solid
  10. customthat was recrystallised (EtOAc-MeOH)

Sources & evidence

ORD record
ord-1f16c7fc5e554056b8f5c4be2643021e
Source dataset
uspto-grants-2007_05
Patent number
US07214681B2

Reaction notes

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