HCID 53651706, compound → HCID 53916947, compound

HRID 248148Notes

Reaction equation

HRID 248148 reaction equation
[CH2:1]([C@@:17]1([CH2:22][O:23]CC2C=CC=CC=2)[NH:20][C:19](=[O:21])[CH2:18]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>[Pd].CO.C(O)(=O)C>[CH2:1]([C@@:17]1([CH2:22][OH:23])[NH:20][C:19](=[O:21])[CH2:18]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 1

HCID 53651706HCID 53651706, compound

Product 1

HCID 53916947HCID 53916947, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

A mixture of 400 mg of (R)-4-hexadecyl-4-[(phenylmethoxy)methyl]-2-azetidinone, 50 mg of 10% palladium-on-carbon and 20 ml of methanol:acetic acid (1:1) is hydrogenated for 16 hours, then filtered and evaporated. The residue is recrystallized from petroleum ether/ethyl acetate, to give 300 mg of the desired compound as a white solid, mp. 82° C.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue is recrystallized from petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-efc7dba28c464001bfd2c5cfbe0c1c63
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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