HCID 68677085, compound → HCID 68678442, compound

HRID 2242181Notes

Reaction equation

HRID 2242181 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[CH:13][C:14]([OH:16])=[O:15])[CH2:10][C@H:9]1[C:17]([N:19]1[CH2:23][CH2:22][S:21][CH2:20]1)=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pt]=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH2:13][C:14]([OH:16])=[O:15])[CH2:10][C@H:9]1[C:17]([N:19]1[CH2:23][CH2:22][S:21][CH2:20]1)=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68677085HCID 68677085, compound

Product 1

HCID 68678442HCID 68678442, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of Example 1C (3.11 g, 0.0090 mol) and platinum oxide (280 mg) in methanol (15 mL) was stirred under an atmosphere of hydrogen at 60 psi pressure for 38 hours at room temperature. Filtration of the catalyst and evaporation of the solvent under reduced pressure provided the desired compound (3.0 g). MS (ESI APCI) m/e 245 (M-Boc+H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 4.37-4.66 (m, 2 H), 3.65 (m, 2 H), 3.09 (s, 2 H), 2.90 (m, 2 H), 2.34-2.44 (m, 1 H), 2.32 (dd, 1 H), 1.91 (m, 1 H), 1.41 (s, 9 H).

Workup

  1. filtrationFiltration of the catalyst and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-a6aa2fdb47354b46b80ec5b663675803
Source dataset
uspto-grants-2010_03
Patent number
US07671076B2

Reaction notes

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