Tetrahydrofuran → HCID 58282810, compound

HRID 339960Notes

Reaction equation

HRID 339960 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCCC1>>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[CH2:10][OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 2734492114873-01-7

Product 1

HCID 58282810HCID 58282810, compound

Procedure

To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3-fluorophenyl)propanoic acid [Aldrich] (3.00 g, 10.6 mmol) in tetrahydrofuran (30 mL, 400 mmol) at 0° C. was added 1.0 M borane-THF complex in tetrahydrofuran (32 mL, 32 mmol). The reaction mixture was stirred at room temperature for 3 hrs, cooled with an ice bath, quenched with AcOH:MeOH (1:5, 10 mL and partitioned between saturated aqueous NaHCO3 and DCM. The aqueous phase was then extracted several times with DCM. The combined organic fractions were dried over Na2SO4 and concentrated under reduced pressure. The residue was used directly for the next reaction. LCMS (ES) m/e 270 (M+H)+.

Workup

  1. temperaturecooled with an ice bath
  2. customquenched with AcOH:MeOH (1:5, 10 mL
  3. custompartitioned between saturated aqueous NaHCO3 and DCM
  4. extractionThe aqueous phase was then extracted several times with DCM
  5. dry with materialThe combined organic fractions were dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was used directly for the next reaction

Sources & evidence

ORD record
ord-38098ceff36e4c3e8c62f43596dd2153
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

Loading…