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

HRID 1873166Notes

Reaction equation

HRID 1873166 reaction equation
[CH:1]1[C:9]2[C:8]3[C:10]([C:18]4[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=4)=[C:11]4[C:16](=[CH:17][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH:15]=[CH:14][CH:13]=[CH:12]4.O[C@@H:26]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:27]([O:29]C)=[O:28]>C(Cl)(Cl)Cl>[CH:1]1[C:9]2[C:8]3[C:10]([C:18]4[CH:19]=[CH:20][C:21]([O:24][C@H:26]([CH2:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:27]([OH:29])=[O:28])=[CH:22][CH:23]=4)=[C:11]4[C:16](=[CH:17][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH:15]=[CH:14][CH:13]=[CH:12]4

Participants

4

Reactant 2

HCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateHCID 107823884-Benzo[b]naphtho[2,3-d]thiophen-11-yl-phenol

Product 1

HCID 54444109(R)-2-[4-(Benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-3-phenyl-propionic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared from 4-benzo[b]naphtho[2,3-d]thiophen-11-yl-phenol (Example 14) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: [a]25/D =-19.09° (8.538 mg/mL, CHCl3); NMR (CDCl3); δ8.30 (s, 1 H), 7.91 (d, J=8 Hz, 1 H), 7.73 (d, J=8 Hz, 1 H), 7.55-7.24 (m, 10 H), 7.14-7.09 (m, 2 H), 7.05 (ddd, J =8, 7, 1 Hz, 1 H), 6.70 (d, J=8 Hz, 1 H), 5.09 (dd, J=8,5 Hz, 1 H,), 3.42 (m, 2 H); MS (EI): [M+] 474 (100%); Anal Calc. for C31H22O3S: C, 78.46, H, 4.67, N, 0.00. Found: C, 77.09, H, 4.60, N, 0.03 Analytical HPLC purity (98.5%).

Sources & evidence

ORD record
ord-d51d72e1d5784df0aa1e7bc5ffcd285e
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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