L-Tartaric acid → HCID 86602622, compound

HRID 1666828Notes

Reaction equation

HRID 1666828 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[F:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][CH:18]=[C:17]2[CH2:21][CH2:22][NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])[CH:26]=1>CO.C(OCC)(=O)C>[C:6]([C@@H:4]([C@H:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])([OH:8])=[O:7].[F:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][CH:18]=[C:17]2[CH2:21][CH2:22][NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][C:33]([F:36])([F:34])[F:35])[CH:26]=1

Participants

5

Reactant 2

HCID 444305L-Tartaric acidHCID 21071661HCID 21071661, compound

Product 1

HCID 86602622HCID 86602622, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add L-(+)-tartaric acid (295 mg, 1.96 mmol) in methanol to a solution of N-(2-(7-fluoro-1H-indol-3-yl)ethyl)-3-(2,2,2-trifluoroethoxy)benzylamine (720 mg, 1.96 mmol) in ethyl acetate. Concentrate under reduced pressure the resulting solution to give a clear colorless oil. Crystallize the oil from diethyl ether to give the title compound: mp 118-119° C. MS (m/e): 367 (M+1), 365 (M−1). Calculated for C19H18F4N2O.C4H6O6: Calcd: C, 53.49; H, 4.68; N, 5.42. Found: C, 53.21; H, 4.55; N, 5.41.

Workup

  1. concentrationConcentrate under reduced pressure the resulting solution
  2. customto give a clear colorless oil
  3. customCrystallize the oil from diethyl ether

Sources & evidence

ORD record
ord-07af8ccfd107433b9c0fecd982f4910a
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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