Boc-Tyr-OMe → (2S)-2-amino-3-{4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}propanoic acid

HRID 2300615Notes

Reaction equation

HRID 2300615 reaction equation
N[C@@H](CC1C=CC(OC[CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25](F)=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=CC=1)C(O)=O.C[O:30][C:31](=[O:49])[C@H:32]([CH2:41][C:42]1[CH:47]=[CH:46][C:45]([OH:48])=[CH:44][CH:43]=1)[NH:33]C(OC(C)(C)C)=O.CC1OC(C2C=CC=CC=2)=NC=1CO>>[NH2:33][C@@H:32]([CH2:41][C:42]1[CH:43]=[CH:44][C:45]([O:48][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:19][C:20]=2[CH3:21])=[CH:46][CH:47]=1)[C:31]([OH:49])=[O:30]

Participants

4

Reactant 3

HCID 7019130Boc-Tyr-OMeHCID 115719324-(Hydroxymethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 70159586(2S)-2-amino-3-(4-{2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}phenyl)propanoic acid

Product 1

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

Procedure

Amino acid Intermediate 54 was prepared as described for the preparation of Intermediate 46. From 187 mg of N-(Boc)-L-Tyrosine methyl ester and 120 mg of Intermediate 8D (with DIAD replacing DEAD) was prepared 116 mg (53% overall yield) of the title compound as a solid. 1H NMR (DMSO-d6, 300 MHz) δ7.89-7.85 (m, 2H), 7.43-7.36 (m, 3H), 7.12 (d, 2H, J=8.5), 6.9 (d, 2H, J=8.5), 4.9 (s, 2H), 3.63 (m, 1H), 3.0 (dd, 1H, J=14.4, 4.5), 2.85 (dd, 1H, J=14.4, 8.1), 2.37 (s, 3H); low resolution MS (ES+)m/e 353.07 (MH+).

Sources & evidence

ORD record
ord-bfb0bd470dcc45db8678f87300ed2dae
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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