Trifluoroacetic acid → HCID 70160166, compound

HRID 2300640Notes

Reaction equation

HRID 2300640 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][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].C(O)(C(F)(F)F)=O.[CH3:35][C:36]([CH2:38][C:39]([C:41]1[O:45][CH:44]=[CH:43][CH:42]=1)=[O:40])=O>>[O:45]1[CH:44]=[CH:43][CH:42]=[C:41]1[C:39](=[O:40])/[CH:38]=[C:36](\[NH: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][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4])/[CH3:35]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 121681,3-Butanedione, 1-(2-furanyl)-HCID 18343040(2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acid

Product 1

HCID 70160166HCID 70160166, compound

Procedure

The title compound was prepared (as described above for the preparation of Example 2) from 630 mg (1.31 mmol) of Intermediate 45 (as the TFA salt) and 200 mg (1.31 mmol) of 1-(2-furyl)-1,3-butadione (purchased from Acros Organics) to yield 230 mg (35% yield) of Example 29 as a light brown solid: TLC (DCM/MeOH (4:1): Rf=0.62; 1H NMR (DMSO-d6, 300 MHz) δ11.07 (d, 1H, J=8.7), 7.88 (m, 2H), 7.69 (d, 1H, J=1.0), 7.48 (m, 3H), 7.09 (d, 2H, J=8.5), 6.86 (m, 3H), 6.52 (d, 1H, J=1.5), 5.33 (s, 1H), 4.13 (t, 2H, J=6.6), 4.03 (m, 1H), 3.14 (m, 1H), 2.87 (t, 2H, J=6.6), 2.70 (dd, 1H, J=13.6, 9.0), 2.34 (s, 3H), 1.62 (s, 3H); low resolution MS (ES+)m/e 501.2 (MH+).

Sources & evidence

ORD record
ord-bc0f935da1dd40ca91eefab51e01e1ad
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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