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

HRID 2300613Notes

Reaction equation

HRID 2300613 reaction equation
C[O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5]C(OC(C)(C)C)=O.[F:22][C:23]([F:40])([F:39])[C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:31][C:32]([CH3:38])=[C:33]([CH2:35][CH2:36]O)[N:34]=2)=[CH:26][CH:25]=1>>[NH2:5][C@@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:36][CH2:35][C:33]2[N:34]=[C:30]([C:27]3[CH:28]=[CH:29][C:24]([C:23]([F:40])([F:22])[F:39])=[CH:25][CH:26]=3)[O:31][C:32]=2[CH3:38])=[CH:18][CH:19]=1)[C:3]([OH:2])=[O:21]

Participants

3

Reactant 2

HCID 7019130Boc-Tyr-OMeHCID 105881722-(5-Methyl-2-(4-(trifluoromethyl)phenyl)oxazol-4-yl)ethanol

Product 1

HCID 18343039(2S)-2-amino-3-[4-(2-{5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3oxazol-4-yl}ethoxy)phenyl]propanoic acid

Procedure

Intermediate 50 was prepared from 185 mg of N-(Boc)-L-Tyrosine methyl ester and 170 mg of Intermediate 13 to yield 130 mg (48% overall yield) of the title compound as a solid: 1H NMR (DMSO-d6, 400 MHz) δ8.16 (d, 2H, J=8.2), 7.92 (d, 2H, J=8.4), 7.21 (d, 2H, J=8.5), 6.93 (d, 2H, J=8.5), 4.25 (t, 2H, J=6.5), 3.1 (dd, 1H, J=14.4, 4.8), 3.0 (t, 2H, J=6.5), 2.76 (dd, 1H, J=14.4, 7.9), 2.46 (s, 3H); low resolution MS (ES+)m/e 434.9 (MH+).

Workup

  1. customto yield

Sources & evidence

ORD record
ord-5c63b83a225d4794af76e74ada973932
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

Loading…