Ammonium Chloride → tert.-butyl (S)-3-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-butanoate

HRID 736923Notes

Reaction equation

HRID 736923 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[NH2:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:15]([CH2:22][CH2:23][C:24]([N:26]2[C@H:30]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:29][O:28][C:27]2=[O:38])=[O:25])=[CH:14][C:13]=1[Cl:39].Br[CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43].[NH4+].[Cl-]>C1COCC1>[NH2:11][C:12]1[C:17]([C:18]([F:19])([F:20])[F:21])=[CH:16][C:15]([CH2:22][C@H:23]([C:24]([N:26]2[C@H:30]([CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:29][O:28][C:27]2=[O:38])=[O:25])[CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])=[CH:14][C:13]=1[Cl:39]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68590943(R)-3-[3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-propionyl]-4-benzyl-oxazolidin-2-one

Product 1

HCID 68592520tert.-butyl (S)-3-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-butanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Under an argon atmosphere 63.24 mL (63.24 mmol) of a sodium-bis(trimethylsilyl)-amide solution (1 M in THF) was added dropwise to a solution of 22.5 g (52.71 mmol) of (R)-3-[3-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-propionyl]-4-benzyl-oxazolidin-2-one in 105 mL THF which had been cooled to −78° C. and the mixture was stirred for 2 h at −78° C. 38.9 mL (263.5 mmol) of tert.butyl bromoacetate were added dropwise to the reaction mixture at −78° C., this was stirred for a further 24 h at −78° C. and then heated to RT. After the addition of 200 mL of a saturated NH4Cl solution the mixture was extracted twice with 300 mL of EtOAc, the combined org. phases were dried over Na2SO4 and evaporated down i. vac. The residue remaining was purified by chromatography on silica gel. The desired product was obtained in the form of a yellow oil.

Workup

  1. stirringthis was stirred for a further 24 h at −78° C.
  2. temperatureheated to RT
  3. extractionwas extracted twice with 300 mL of EtOAc
  4. dry with materialphases were dried over Na2SO4
  5. customevaporated down i
  6. customThe residue remaining was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4053ff63a8b3459eafa531d30f92baf3
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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