Trifluoroacetic acid → HCID 67151550, compound

HRID 1805233Notes

Reaction equation

HRID 1805233 reaction equation
FC(F)(F)C(O)=O.CC1(C)[N:13](C(O)=O)[C@@H:12](/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)[CH2:11][O:10]1.[OH-].[Na+]>O.C(#N)C>[NH2:13][C@@H:12](/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)[CH2:11][OH:10]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86653292HCID 86653292, compound

Product 1

HCID 67151550HCID 67151550, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of trifluoroacetic acid (4.9 ml) in water (24 ml) was added (S)-2,2-dimethyl-4-[(E)-2-(4-nitro-phenyl)-vinyl]-oxazolidine-3-carboxylic acid tent-butyl ester (Example 14(a)) (5.0 g) in acetonitrile (4.0 ml). After stirring at 80° C. for 4 hours, the reaction mixture was cooled to room temperature and the solution basified to pH>11 by dropwise addition of a 1N solution of sodium hydroxide The mixture was extracted three times with ethyl acetate, the combined organic layers were dried (MgSO4) and concentrated in vacuo to yield (E)-(S)-2-Amino-4-(4-nitro-phenyl)-but-3-en-1-ol as a brown oil (2.5 g). 1H-NMR (300 MHz, CDCl3, δ); 8.23-8.11 (m, 2H), 8.54-8.47 (m, 2H), 7.67 (d, J=16 Hz, 1H), 6.7 (dd, J=16 and 8 Hz, 1H). 3.78-3.69 (m, 2H), 3.58-3.42 (m, 1H).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionwas extracted three times with ethyl acetate
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c876da3933074f46bb1d027fedced620
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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