(S)-methyl 2-hydroxy-3-phenylpropanoate → 4-(3-Carboxymethoxy-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy-3-phenyl-propionic acid

HRID 1873167Notes

Reaction equation

C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:13]3[C:14]([C:22]4[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=4)=[C:15]4[C:20](=[CH:21][C:12]=3[S:11][C:10]=2[CH:29]=1)[CH:19]=[CH:18][CH:17]=[CH:16]4.O[C@@H:32]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:33]([O:35]C)=[O:34]>>[C:3]([CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:13]3[C:14]([C:22]4[CH:23]=[CH:24][C:25]([O:28][CH:32]([CH2:37][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[C:33]([OH:35])=[O:34])=[CH:26][CH:27]=4)=[C:15]4[C:20](=[CH:21][C:12]=3[S:11][C:10]=2[CH:29]=1)[CH:19]=[CH:18][CH:17]=[CH:16]4)([OH:2])=[O:30]

Participants

Reactant 2

HCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoate

HCID 54268796HCID 54268796, compound

Product 1

HCID 867557104-(3-Carboxymethoxy-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy-3-phenyl-propionic acid

Procedure

Prepared from of [11 -(4-hydroxy-phenyl)-benzo[b]naphtho[2,3-d]thiophen-3-yloxy ]-acetic acid methyl ester (Example 72) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: mp: 191-201° C.: NMR (DMSO-d6); δ13.1 (broad s, 2 H), 8.45 (s, 1 H), 8.01 (d, J=8 Hz, 1 H), 7.55-7.25 (m, 11H), 7.16 (d, J =9 Hz, 2 H), 6.67 (dd, J=9, 2Hz, 1 H), 6.49 (d, J=9 Hz, 1 H), 5.18 (dd, J=7,4Hz, 1 H), 4.74 (s, 2 H), 3.28 (dd, J=7, 4 Hz, 1 H), 3.21 (dd, J=14, 7 Hz, 1 H); MS (EI): 458 (80%, M+); Anal. Calc. for C33H24O6S: C, 72.25, H, 4.41, N, 0.00. Found: C, 69.57, H, 4.15, N, 0.32; Analytical HPLC :92% purity.

Sources & evidence

ORD record: ord-7cdbeda4c322476c8c6a9cbdcb75301b
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06110962

Reaction notes

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