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

HRID 2300614Notes

Reaction equation

HRID 2300614 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.[CH:22]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:33][C:34]([CH3:40])=[C:35]([CH2:37][CH2:38]O)[N:36]=2)=[CH:28][CH:27]=1)([CH3:24])[CH3:23]>>[NH2:5][C@@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:38][CH2:37][C:35]2[N:36]=[C:32]([C:29]3[CH:30]=[CH:31][C:26]([O:25][CH:22]([CH3:23])[CH3:24])=[CH:27][CH:28]=3)[O:33][C:34]=2[CH3:40])=[CH:18][CH:19]=1)[C:3]([OH:2])=[O:21]

Participants

3

Reactant 2

HCID 7019130Boc-Tyr-OMeHCID 180035882-[2-(4-Isopropoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethanol

Product 1

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

Procedure

Intermediate 51 was prepared from 598 mg of N-(Boc)-L-Tyrosine methyl ester and 530 mg of Intermediate 14 to yield 540 mg (63% overall yield) of the title compound as a solid. 1H NMR (DMSO-d6, 400 MHz) δ7.77 (d, 2H, J=8.7), 7.12 (d, 2H, J=8.6), 6.9 (d, 2H, J=8.9), 6.82 (d, 2H, J=8.5), 4.65 (hept, 1H, J=6.0), 4.13 (t, 2H, J=6.6), 3.0 (dd, 1H, J=14.4, 4.5), 2.85 (t, 2H, J=6.4), 2.76 (dd, 1H, J=14.4, 8.0), 2.31 (s, 3H), 1.25 (d, 6H, J=6.0); low resolution MS (ES+)m/e 425.2 (MH+).

Workup

  1. customto yield

Sources & evidence

ORD record
ord-adec33cbef4a4987ababa4f251b8f3b3
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

Loading…