Water → HCID 86756495, compound

HRID 1530900Notes

Reaction equation

HRID 1530900 reaction equation
[CH3:1][O:2][C:3](=[O:43])[N:4]([CH2:28][C:29]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=1)[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=2)[N:8](C(=O)C(F)(F)F)[C@@H:7]([CH:25]2[CH2:27][CH2:26]2)[CH2:6]1.O1CCCC1.[OH-].[Li+].O>CO>[F:38][C:35]([F:36])([F:37])[C:33]1[CH:34]=[C:29]([CH:30]=[C:31]([C:39]([F:41])([F:42])[F:40])[CH:32]=1)[CH2:28][N:4]([C:3]([O:2][CH3:1])=[O:43])[C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=2)[NH:8][C@@H:7]([CH:25]2[CH2:27][CH2:26]2)[CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86756496HCID 86756496, compound

Product 1

HCID 86756495HCID 86756495, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

cis-(3,5-Bis-trifluoromethyl-benzyl)-(2-cyclopropyl-1-trifluoroacetyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid methyl ester (Example 47) (900 mg, 1.41 mmol) was dissolved in 20 mL of methanol and 60 mL of tetrahydrofuran before adding lithium hydroxide (1.6 mL of 1.0M aqueous solution, 1.6 mmol) to the solution. After 2 h at room temperature, 100 mL of water was added and the mixture extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with 50 mL of brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title product (740 mg) as a colorless solid which was used without further purification. MS m/z 542 (M+2)+; 1H NMR (CDCl3) δ 0.2 (m, 2H), 0.55 (m, 2H), 0.8 (m, 1H).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic extracts were washed with 50 mL of brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eabc362dbf29465ab916194f5ab893e2
Source dataset
uspto-grants-2001_03
Patent number
US06197786B1

Reaction notes

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