HCID 25136280, compound → HCID 58864235, compound

HRID 1177803Notes

Reaction equation

HRID 1177803 reaction equation
[CH3:1][O:2][C:3]([C@H:5]([NH:17]C(=O)OCC1C=CC=CC=1)[CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:14][C:13](=[O:15])[NH:12][C:11]=2[CH:16]=1)=[O:4].[H][H]>[Pd].CO>[NH2:17][C@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:14][C:13](=[O:15])[NH:12][C:11]=2[CH:16]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

5

Reactant 2

HCID 25136280HCID 25136280, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58864235HCID 58864235, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl(R)-1-(methoxycarbonyl)-2-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-6-yl)ethylcarbamate (265 mg, 0.72 mmol) and 10% palladium on carbon (30 mg) in methanol (15 mL) were agitated for 1.5 h under 50 psi hydrogen using a Parr apparatus. The reaction mixture was purged with 3 vacuum/nitrogen purge cycles. The reaction mixture was then filtered through a pad of Celite® and the pad was rinsed with several portions of methanol. The methanol filtrate was evaporated to give the title compound (168 mg, quantitative yield). 1H-NMR (CD3OD, 300 MHz) δ 6.97 (d, J=8.1 Hz, 1H), 6.87 (s, 1H), 6.86 (d, J=8.2 Hz, 1H), 3.71-3.64 (m, 1H), 3.67 (s, 3H), 3.04-2.89 (m, 2H). LC/MS: tR=0.87 min, 236 (MH)+.

Workup

  1. customThe reaction mixture was purged with 3 vacuum/nitrogen
  2. custompurge cycles
  3. filtrationThe reaction mixture was then filtered through a pad of Celite®
  4. washthe pad was rinsed with several portions of methanol
  5. customThe methanol filtrate was evaporated

Sources & evidence

ORD record
ord-14813d1a4a794546beb7c80340656114
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

Loading…