Methanol → 3-Amino-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

HRID 2075811Notes

Reaction equation

HRID 2075811 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH:7](O)[CH:8]([NH:22]C(OCC1C=CC=CC=1)=O)[CH2:9][CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])([CH3:4])([CH3:3])[CH3:2].C[OH:36]>>[C:1]([O:5][C:6](=[O:34])[CH2:7][CH:8]([NH2:22])[CH:9]([OH:36])[CH2:10][O:11][C:12]1[C:17]([F:18])=[C:16]([F:19])[CH:15]=[C:14]([F:20])[C:13]=1[F:21])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 866130753-Benzyloxycarbonylamino-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

Product 1

HCID 750793883-Amino-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl esterYield 99%

Procedure

Composition 13 (163 mg, 0.33 mmol) and MeOH (˜15 mL) was added to a dry round bottom flask equipped with a magnetic stir bar. The flask was purged several times with N2 and a catalytic amount of 10% Pd on C was carefully added to the reaction flask. The resulting black heterogeneous mixture was evacuated under vacuum and charged twice with H2 via a rubber balloon with constant stirring. The reaction was stirred at room temperature for 1.5 h and upon completion was filtered thru a pad of Celite, concentrated in vacuo to give 14 (115 mg, 0.32 mmol, 99% yield) as a sticky off-white solid. ESMS: 354.8 (M+H), 376.2 (M+Na+).

Workup

  1. customequipped with a magnetic stir bar
  2. customThe flask was purged several times with N2
  3. additiona catalytic amount of 10% Pd on C was carefully added to the reaction flask
  4. customThe resulting black heterogeneous mixture was evacuated under vacuum
  5. additioncharged twice with H2 via a rubber balloon with constant stirring
  6. filtrationwas filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-659f70638ff04e13ac1ed13d91bb3399
Source dataset
uspto-grants-2011_04
Patent number
US07923433B2

Reaction notes

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