Lithium hydroxide, monohydrate → HCID 86711857, compound

HRID 623773Notes

Reaction equation

HRID 623773 reaction equation
O[Li].O.[CH2:4]([N:11]1[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][C:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[C:12]1[C:27]([N:29]([CH2:31][C:32]([CH3:38])([CH3:37])[C:33]([O:35]C)=[O:34])[CH3:30])=[O:28])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.OS([O-])(=O)=O.[K+]>O.C1COCC1>[CH2:4]([N:11]1[C:15]([C:16]([F:19])([F:18])[F:17])=[CH:14][C:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[C:12]1[C:27]([N:29]([CH2:31][C:32]([CH3:38])([CH3:37])[C:33]([OH:35])=[O:34])[CH3:30])=[O:28])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrate2×HCID 516920Potassium bisulfateHCID 86711858HCID 86711858, compound

Product 1

HCID 86711857HCID 86711857, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of LiOH H2O (214 mg, 5.11 mmol) in H2O (3 mL) was added to a stirred solution of methyl 3-(1-benzyl-3-(4-chlorophenyl)-N-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxamido)-2,2-dimethylpropanoate (259 mg, 0.511 mmol) in THF (3 mL). The reaction mixture was stirred at room temperature overnight. An extra portion of LiOH H2O (107 mg, 2.55 mmol) was added, followed by the addition of H2O (11 mL) and THF (11 mL). The reaction mixture was stirred at room temperature for 2 d and then acidified with aqueous 0.5 M KHSO4 (10 mL). The product was extracted with DCM (3×20 mL). The organic layers were combined and washed with brine (3×10 mL). The combined organic layers were dried on Na2SO4 and filtered. Solvents were removed in vacuo to give the desired product (233 mg, 93%) as a white foam.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 d
  2. extractionThe product was extracted with DCM (3×20 mL)
  3. washwashed with brine (3×10 mL)
  4. customThe combined organic layers were dried on Na2SO4
  5. filtrationfiltered
  6. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-8c8a5035f69e4a38916569d48e15864f
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

Loading…