Benzoylacetone → (2S)-2-{[(Z)-1-methyl-3-oxo-3-phenyl-1-propenyl]amino}-3-{4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}propanoic acid

HRID 2300651Notes

Reaction equation

HRID 2300651 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[C:27]([CH2:35][C:36](=O)[CH3:37])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH3:37]/[C:36](/[NH:1][C@@H:2]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:18][C:19]=2[CH3:20])=[CH:11][CH:12]=1)[C:3]([OH:5])=[O:4])=[CH:35]/[C:27](=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 7166BenzoylacetoneHCID 69835737(2S)-2-amino-3-{4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}propanoic acid

Product 1

HCID 69835553(2S)-2-{[(Z)-1-methyl-3-oxo-3-phenyl-1-propenyl]amino}-3-{4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}propanoic acid

Procedure

The title compound was prepared (as described above for the preparation of example 1) from a suspension of 113 mg (0.32 mmol) of Intermediate 54 and 52 mg (0.32 mmol) of benzoylacetone to yield 44 mg (28%) of example 54: TLC (DCM/MeOH, 4/1): Rf=0.55; 1H NMR (DMSO-d6, 300 MHz) δ11.43 (d, 1H, J=9.0), 7.92-7.88 (m, 2H), 7.8 (m, 2H), 7.48 (m, 3H), 7.38-7.38 (m, 3H), 7.16 (d, 2H, J=8.4), 6.9 (d, 2H, J=8.4), 5.53 (s, 1H), 4.91 (s, 1H), 4.15 (m, 1H), 3.2 (m, 2H), 2.83-2.74 (m, 1H), 2.37 (s, 3H), 1.67 (s, 3H); low resolution MS (ES+)m/e 497.07 (MH+).

Workup

  1. customas described above for the preparation of example 1)

Sources & evidence

ORD record
ord-76cc977c62404002be6ee84565fd986a
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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