Tetrahydrofuran → HCID 18313811, compound

HRID 381519Notes

Reaction equation

HRID 381519 reaction equation
C([O:8][C:9](=[O:36])[CH:10]([NH:15][C:16](=[O:35])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])=[O:26])=[CH:20][CH:19]=1)[CH2:11]C(C)C)C1C=CC=CC=1.[CH2:37]1[CH2:41]OC[CH2:38]1>CO.[OH-].[OH-].[Pd+2]>[CH3:11][C:10]([NH:15][C:16](=[O:35])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])=[O:26])=[CH:20][CH:19]=1)([CH2:38][CH2:37][CH3:41])[C:9]([OH:8])=[O:36]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 18682347HCID 18682347, compound

Product 1

HCID 18313811HCID 18313811, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-methyl-2-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-pentanoic acid benzyl ester (4.0 g) and palladium hydroxide on carbon (1.0 g) in 200 ml of MeOH and 200 ml of THF was shaken on a Parr apparatus under 30 p.s.i. of H2. After 2 h the mixture was filtered through celite and the filtrate was concentrated under reduced pressure to give 3.6 g of the title compound as a white solid. MS [M+1]+ 398.3; 1H nmr (400 MHz, DMSO-d6) δ0.79 (d, J=6.4 Hz, 3H), 0.86 (d, J=6.4 Hz, 3H), 1.44-1.63 (m, 3H), 2.21 (s, 3H), 3.36-3.40 (m, 2H), 4.15-4.20 (m, 1H), 6.91 (t, 1H), 7.09-7.14 (m, 4H), 7.33 (d, 2H), 7.81 (d, 1H), 7.89 (s, 1H), 8.26 (d, 1H), 8.97 (s, 1H).

Workup

  1. filtrationAfter 2 h the mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0b2d8188c4a8428390b16f3cdf3fabd4
Source dataset
uspto-grants-2001_10
Patent number
US06306887B1

Reaction notes

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