Trifluoroacetic acid → HCID 70159644, compound

HRID 2300642Notes

Reaction equation

HRID 2300642 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.[N:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41](=[O:46])[CH2:42][C:43](=O)[CH3:44]>>[CH3:44]/[C:43](/[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])=[CH:42]/[C:41](=[O:46])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][N:35]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 127072211-(Pyridin-2-yl)butane-1,3-dioneHCID 18343040(2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acid

Product 1

HCID 70159644HCID 70159644, compound

Procedure

The title compound was prepared (as described above for the preparation of Example 2) from 441 mg (0.92 mmol) of Intermediate 45 (as the TFA salt) and 150 mg (0.92 mmol) of Intermediate 35 to yield 240 mg of Example 34: TLC (DCM/MeOH, 4/1): Rf=0.46; 1H NMR (DMSO-d6, 400 MHz) δ11.49 (d, 1H, J=9.2), 8.52 (d, 1H, J=4.8), 7.90 (m, 4H), 7.47 (m, 4H), 7.11 (d, 2H, J=8.4), 6.80 (d, 2H, J=8.4), 6.13 (s, 1H), 4.12 (m, 3H), 3.16 (m, 2H), 2.87 (t, 2H, J=6.4), 2.77 (dd, 1H, J=13.6, 9.2), 2.34 (s, 3H), 1.71 (s, 3H); low resolution MS (ES−)m/e 510.1 (M-H).

Sources & evidence

ORD record
ord-4fd1278b9b9e4ee79513fe42cda7f106
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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