N-[tert-Butoxy(hydroxy)methylidene]-3-(trifluoromethyl)phenylalaninato → HCID 66635534, compound

HRID 339952Notes

Reaction equation

HRID 339952 reaction equation
C(OC([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[C:10](O)=[O:11])=O)(C)(C)C>O1CCCC1>[NH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=1)[CH2:10][OH:11]

Participants

3

Reactant 1

HCID 7020838N-[tert-Butoxy(hydroxy)methylidene]-3-(trifluoromethyl)phenylalaninato

Product 1

HCID 66635534HCID 66635534, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-[3-(trifluoromethyl)phenyl]-propanoic acid (Aldrich) (10.00 g, 30.00 mmol) in tetrahydrofuran (25 mL) with stirring, 1.0 M borane-THF complex in THF (100.0 mL, 100.0 mmol) (newly opened) was added dropwise to keep the internal temperature at 0° C. (release gas, about 15 min). After addition the reaction was stirred at room temperature (rt) for 6 hrs, cooled down with ice-bath, quenched with AcOH:MeOH (1:5, 50 mL), and partitioned between saturated aqueous NaHCO3 and DCM, dried over sodium sulfate, filtered, and evaporated under reduced pressure to give an oil residue, which was purified by combi-flash chromatography to give the desired intermediate. LC-MS found: 320.1 (M+H)+.

Workup

  1. additionwas added dropwise
  2. customat 0° C.
  3. custom(release gas, about 15 min)
  4. additionAfter addition the reaction
  5. temperaturecooled down with ice-bath
  6. customquenched with AcOH:MeOH (1:5, 50 mL)
  7. custompartitioned between saturated aqueous NaHCO3 and DCM
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. customto give an oil residue, which
  12. customwas purified by combi-flash chromatography

Sources & evidence

ORD record
ord-96cff03cff834f388b9f3d6a9bbe271f
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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