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

HRID 2300648Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[C:32]([CH2:40][C:41](=O)[CH3:42])(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH:29]([O:28][C:25]1[CH:24]=[CH:23][C:22]([C:18]2[O:19][C:20]([CH3:21])=[C:16]([CH2:15][CH2:14][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][C@H:2]([NH:1]/[C:41](/[CH3:42])=[CH:40]\[C:32](=[O:39])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:3]([OH:5])=[O:4])=[CH:12][CH:11]=3)[N:17]=2)=[CH:27][CH:26]=1)([CH3:31])[CH3:30]

Participants

Reactant 2

HCID 7166Benzoylacetone

HCID 70160210(2S)-2-amino-3-(4-{2-[2-(4-isopropoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}phenyl)propanoic acid

Product 1

HCID 69836138(2S)-3-(4-{2-[2-(4-isopropoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}phenyl)-2-{[(Z)-1-methyl-3-oxo-3-phenyl-1-propenyl]amino}propanoic acid

Procedure

The title compound was prepared (as described above for the preparation of Example 2) from 75 mg (0.18 mmol) of Intermediate 51 and 32 mg (0.194 mmol) of benzoylacetone to yield 55 mg of Example 44: TLC (DCM/MeOH (4:1): Rf=0.50; 1H NMR (DMSO-d6, 400 MHz) δ11.5 (d, 1H, J=9.0), 7.85 (m, 4H), 7.45 (m, 3H), 7.18 (d, 2H, J=8.4); 7.06 (d, 2H, J=8.8), 6.87 (d, 2H, J=8.5), 5.82 (s, 1H), 4.74 (m, 1H), 4.19 (t, 2H, J=6.6), 4.1 (m, 1H), 3.19 (m, 1H), 2.92 (t, 2H, J=6.6), 2.81 (dd, 1H, J=13.9. 9.1), 2.36 (s, 3H), 1.74 (s, 3H), 1.34 (d, 6H, J=6.0); low resolution MS (ES−)m/e 567.2 (M-)

Sources & evidence

ORD record: ord-3e2a6a5321304ee2aee540c72994e809
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498174B1

Reaction notes

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