Water → HCID 68864362, compound

HRID 1725894Notes

Reaction equation

HRID 1725894 reaction equation
[CH2:1]([C:5]1[C:6]([CH3:31])=[C:7]([C:18]([NH:21][S:22]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)(=[O:24])=[O:23])=[CH:19][CH:20]=1)[C:8]([O:10]CC1C=CC=CC=1)=[O:9])[CH2:2][CH2:3][CH3:4].O>CO.C1COCC1.[Pd]>[CH2:1]([C:5]1[C:6]([CH3:31])=[C:7]([C:18]([NH:21][S:22]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)(=[O:23])=[O:24])=[CH:19][CH:20]=1)[C:8]([OH:10])=[O:9])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 962WaterHCID 68863966HCID 68863966, compound

Product 1

HCID 68864362HCID 68864362, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 114A (87 mg) in methanol (4 mL), THF (4 mL), and water (1 mL) was treated with 5% Pd/C (100 mg), stirred under a hydrogen atmosphere for 1 hour, and filtered through diatomaceous earth (Celite®), and concentrated to provide the desired product (47 mg). 1H NMR (DMSO-d6) δ 0.89 (t, 3H), 1.29-1.34 (m, 2H), 1.40-1.45 (m, 2H), 2.21 (s, 3H), 2.52 (t, 2H), 6.81 (d, 1H), 7.07 (t, 1H), 7.58 (t, 1H), 8.07 (d, 1H), 8.77 (d, 1H), 8.83 (s, 1H); MS (ESI(−)) m/e 347 (M−H)−.

Workup

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ea99a9f57a0d41a29a1afeca42c6169d
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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