Water → HCID 66705917, compound

HRID 2276383Notes

Reaction equation

HRID 2276383 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[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>[NH2:8][C@H:12]([CH2:11][OH:10])[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:30])[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 66705951HCID 66705951, compound

Product 1

HCID 66705917HCID 66705917, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (S)-4-{2-[4-(4-chloro-benzoylamino)-phenyl]-ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (438 mg) in acetonitrile (5 ml) were added water (4 ml) and trifluoroacetic acid (0.29 ml). The mixture was heated at 80° C. for 4.5 h. The mixture was then cooled to room temperature and poured into 1 M aq. NaOH and extracted twice with EtOAc/THF. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford N-[4-((S)-3-amino-4-hydroxy-butyl)-phenyl]-4-chloro-benzamide (255 mg, 84%) a white solid. MS (ISP): 321.2 ([{37Cl}M+H]+), 319.2 ([{35Cl}M+H]).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionextracted twice with EtOAc/THF
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49388cdf7cf64b42a7069f906b6deaa7
Source dataset
uspto-grants-2015_09
Patent number
US09132136B2

Reaction notes

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