HCID 18682344, compound → HCID 18313858, compound

HRID 381516Notes

Reaction equation

HRID 381516 reaction equation
C([O:8][C:9](=[O:42])[CH2:10][CH:11]1[O:15][C:14]([CH:16]([NH:21][C:22](=[O:41])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])=[O:32])=[CH:26][CH:25]=2)[CH2:17][CH:18]([CH3:20])[CH3:19])=[N:13][CH2:12]1)C1C=CC=CC=1>C1COCC1.CO.[OH-].[Pd+2].[OH-]>[CH3:19][CH:18]([CH3:20])[CH2:17][CH:16]([C:14]1[O:15][CH:11]([CH2:10][C:9]([OH:42])=[O:8])[CH2:12][N:13]=1)[NH:21][C:22](=[O:41])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])=[O:32])=[CH:26][CH:25]=1

Participants

5

Reactant 1

HCID 18682344HCID 18682344, compound

Product 1

HCID 18313858HCID 18313858, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [2-(3-methyl-1-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-butyl)-4,5-dihydrooxazol-5-yl]-acetic acid benzyl ester (120 mg) and palladium hydroxide (40 mg) in 10 ml of THF and 10 ml of MeOH was shaken on a Parr Apparatus under 30 p.s.i. H2 for 2 h. The mixture was filtered through Celite and the filtrate concentrated under reduced pressure. The residue was suspended in EtOAc and concentrated under reduced pressure. Trituration with hot EtOAc gave 93 mg of the title compound as a light pink solid. MS [M+1]+ 481.3; 1H nmr (400 MHz, DMSO-d6) δ0.77-0.87 (m, 6H), 1.39-1.59 (m, 3H), 2.10-2.33 (m, 4H, including s at 2.21, 3H), 2.40-5.08 (m, 7H, including q at 3.36, J=14.2 Hz, 2H), 6.90 (t, J=7.4 Hz, 1H), 7.08-7.14 (m, 4H), 7.35 (d, J=6.8 Hz, 2H), 7.79 (d, J=8.1 Hz, 1H), 7.95-8.45 (m, 2H), 9.13-9.23 (m, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated under reduced pressure
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bfe1b7f8c6cd4070863904bfd592f4b7
Source dataset
uspto-grants-2001_10
Patent number
US06306887B1

Reaction notes

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