Water → HCID 67151519, compound

HRID 1805226Notes

Reaction equation

HRID 1805226 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([C:23](=[O:31])[C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[CH3:22])=[CH:17][CH:16]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.O.FC(F)(F)C(O)=O.[OH-].[Na+]>C(#N)C.C(OCC)(=O)C>[NH2:8][C@H:12]([CH2:11][OH:10])[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]([CH3:22])[C:23](=[O:31])[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67151549HCID 67151549, compound

Product 1

HCID 67151519HCID 67151519, compoundYield 122.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

(S)-4-(2-{4-[(4-Chloro-benzoyl)-methyl-amino]-phenyl}-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (110 mg) was dissolved in acetonitrile (1 ml) and water (2 ml) at room temperature before addition of trifluoroacetic acid (140 μl). The reaction mixture was heated to 80° C. and then stirred for 3 hours. After cooling to room temperature, ethyl acetate (4 ml) was added and the solution basified to pH 14 by addition of 2M aqueous sodium hydroxide. The mixture was stirred for 5 minutes and then extracted four times with ethyl acetate, dried over Na2SO4, filtered and concentrated in vacuo to afford N-[4-((S)-3-amino-4-hydroxy-butyl)-phenyl]-4-chloro-N-methyl-benzamide (95 mg) as a light yellow viscous oil. MS (ISP): 333.4 ([M+H]+).

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringThe mixture was stirred for 5 minutes
  3. extractionextracted four times with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46d27e35505448b5ac85065751d541ec
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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