HCID 10325385, compound → HCID 10454855, compound

HRID 2260003Notes

Reaction equation

HRID 2260003 reaction equation
[C:1]([O:5][P:6]([C:13]([F:38])([F:37])[C:14]1[CH:36]=[CH:35][C:17]([CH2:18][CH:19]([C:31]([O:33][CH3:34])=[O:32])[NH:20]C(OCC2C=CC=CC=2)=O)=[CH:16][CH:15]=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)Cl.CO>CO.[Pd]>[C:9]([O:8][P:6]([C:13]([F:38])([F:37])[C:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH:19]([C:31]([O:33][CH3:34])=[O:32])[NH2:20])=[CH:35][CH:36]=1)([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])([CH3:10])([CH3:11])[CH3:12]

Participants

5

Reactant 2

HCID 10325385HCID 10325385, compoundHCID 21584188Chloroform methanol

Product 1

HCID 10454855HCID 10454855, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyloxycarbonyl-protected 11 (45 mg, 0.081 mmol) in MeOH (0.8 mL) was stirred at ambient temperature under 1 atm of H2 over 10% Pd, C (9 mg). After 2.5 hours the reaction mixture was filtered through silica gel and taken to dryness in vacuo to yield crude 12 quantitatively. Pure 12 (60% yield) was obtained by silica gel chromatography [CHCl3 :MeOH (20:1)].

Workup

  1. filtrationAfter 2.5 hours the reaction mixture was filtered through silica gel
  2. customto yield crude 12 quantitatively

Sources & evidence

ORD record
ord-45f655ed7900450eaabc3d0e7265623b
Source dataset
uspto-grants-1995_12
Patent number
US05475129

Reaction notes

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