Acetic Acid → HCID 66618203, compound

HRID 1009981Notes

Reaction equation

HRID 1009981 reaction equation
[CH:1]1([O:6][C:7](=[O:25])[C@@H:8]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C>C(O)(C)C.O=[Pt]=O>[CH:1]1([O:6][C:7](=[O:25])[C@@H:8]([NH:17][C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:9][CH:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 57994321HCID 57994321, compound

Product 1

HCID 66618203HCID 66618203, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 3776IsopropanolSolvent

Procedure

(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid cyclopentyl ester (Scheme 12) (2.35 g, 9.5 mmol) in isopropanol (40 ml) was placed in a glass insert (120 ml volume). PtO2 (0.47 g, 2.1 mmol) was added to the glass insert which was placed in a hydrogenation bomb. Acetic acid (3 ml) was placed in a glass vial in the bomb next to the glass insert. The bomb was sealed and the reaction stirred for 16 h under an atmosphere of hydrogen (5 bar pressure). The reaction mixture was filtered through celite and washed with isopropanol. The solvent was removed in vacuo and azeotroped with THF to remove excess isopropanol to furnish the 2.58 g (quantitative yield) of the desired product.

Workup

  1. customThe bomb was sealed
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed with isopropanol
  4. customThe solvent was removed in vacuo
  5. customazeotroped with THF
  6. customto remove excess isopropanol

Sources & evidence

ORD record
ord-20ac2c4dbbb8471db3d6ecff0ea55cf7
Source dataset
uspto-grants-2011_07
Patent number
US07973181B2

Reaction notes

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