Acetic Acid → HCID 56981804, compound

HRID 1738921Notes

Reaction equation

HRID 1738921 reaction equation
C(OC(=O)[N:7](C(=O)C)[C@H:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[C@H:10]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)[CH2:9]1)(C)(C)C.C([Li])CCC.C(O)(=O)C>CO.CCCCCC>[F:24][C:21]([F:22])([F:23])[C:19]1[CH:20]=[C:15]([CH:16]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:18]=1)[C:14]([N:11]1[CH2:12][CH2:13][C@H:8]([NH2:7])[CH2:9][C@H:10]1[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1)=[O:29]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 57114603HCID 57114603, compoundHCID 178418339Butyllithium

Product 1

HCID 56981804HCID 56981804, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

A solution of 200 mg (0.32 mmol) of (2R*,4S*)-N-acetyl-N-[1-(3,5-bis-trifluoromethyl-benzoyl)-2-(4-nitro-benzyl)-piperidin-4-yl]-carbamic acid tert-butyl ester is added in 5 ml of methanol to a solution, stirred under an inert gas, of 0.04 ml (0.06 mmol) of n-butyllithium in hexane (1.6 M). After 1 hour, 5 mg (0.08 mmol) of acetic acid are added and the mixture is concentrated to dryness by evaporation. The residue is taken up in 2 ml of methylene chloride and 1.2 ml of trifluoroacetic acid and the mixture is stirred for 2.5 hours at room temperature. The mixture is diluted with methylene chloride and washed with 2 N sodium hydroxide solution. The organic phase is dried over sodium sulfate, filtered and concentrated to dryness. The title compound is obtained in the form of a beige foam. TLC: dichloromethane/methanol/conc. ammonia (90:9:0.5) Rf =0.38. 1H-NMR (200 MHz, D2O): rotameric mixture; δ: 8.28-8.08 (m, 2H), 7.94-7.79 (m, 1H), 7.60-7.40 (m, 2H), 7.21-7.02 (m, 2H), 5.40-5.22 (m, 0.5H), 4.85-4.68 (m, 0.5H), 4.00-3.86 (m, 0.5H), 3.56-3.00 (m, 3H), 2.82-2.70 (m, 0.5H), 2.20-1.86 (m, 2H), 1.6-1.2 (m, 2H).

Workup

  1. concentrationthe mixture is concentrated to dryness by evaporation
  2. additionThe mixture is diluted with methylene chloride
  3. washwashed with 2 N sodium hydroxide solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1b5efa156b5244e1b34449bf23e0ef00
Source dataset
uspto-grants-1999_10
Patent number
US05965562

Reaction notes

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