Ammonia → (S)-4-Methylsulfanyl-2-{[5-(pyridin-3-ylmethoxy)-biphenyl-2-carbonyl]-amino}-butyric acid

HRID 2121210Notes

Reaction equation

C[O:2][C:3](=[O:32])[C@H:4]([CH2:28][CH2:29][S:30][CH3:31])[NH:5][C:6](=[O:27])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:9][C:8]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N>>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][O:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([NH:5][C@H:4]([C:3]([OH:32])=[O:2])[CH2:28][CH2:29][S:30][CH3:31])=[O:27])=[C:8]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:9]=2)[CH:16]=1

Participants

Reactant 2

HCID 222Ammonia

HCID 53751775[4-(3-Pyridylmethyloxy)-2-phenylbenzoyl]methionine methyl ester

Product 1

HCID 10812835(S)-4-Methylsulfanyl-2-{[5-(pyridin-3-ylmethoxy)-biphenyl-2-carbonyl]-amino}-butyric acid

Procedure

The desired compound was prepared by saponification of the compound of Example 240F using the procedure of Example 159. 1H NMR (300 MHz, DMSO-d6) δ 8.69 (bs, 1H), 8.55 (bd, 1H), 8.39 (d, 1H), 7.88 (dt, 1H), 7.40 (m, 6H), 7.07 (dd, 1H), 7.03 (d, 1H), 5.17 (s, 2H), 4.28 (ddd, 1H), 2.25 (m, 2H), 2.00 (s, 3H), 1.84 (m, 2H). MS (CI, NH3) m/e 454 (M+NH4)+, 437 (M+H)+, 419, 320, 288. Anal calcd for C24H24N2O4S (+0.23 H2O): C, 65.42; H, 5.59; N, 5.99. Found: C, 65.41; H, 5.42; N, 5.99.

Sources & evidence

ORD record: ord-7a2936e1c1c4492e8ddd96129f18f22e
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693123B2

Reaction notes

Loading…