(S)-methyl 2-hydroxy-3-phenylpropanoate → HCID 18687886, compound

HRID 1873182Notes

Reaction equation

HRID 1873182 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[S:20][C:16]=3[C:15]([CH3:25])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([Br:26])[C:3]=1[OH:27].O[C@@H:29]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30]([O:32]C)=[O:31]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[S:20][C:16]=3[C:15]([CH3:25])=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([Br:26])[C:3]=1[O:27][CH:29]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30]([OH:32])=[O:31]

Participants

4

Reactant 2

HCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateHCID 18687796HCID 18687796, compound

Product 1

HCID 18687886HCID 18687886, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared from 2,6-dibromo-4-(6-methyl-benzo[b]naphtho[2,3-d]thiophen- 11-yl)-phenol (Example 62) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: mp 117-122° C.: [a]D25=+34.13° (9.963 mg/mL CHCl3); NMR (DMSO-d6): δ8.17 (d, J=8 Hz, 1 H), 7.81 (d, J=8 Hz, 1 H), 7.63-7.58 (m, 1 H), 7.57 (dd, J=6, 2 Hz, 2 H), 7.52-7.46 (m, 2 H), 7.42-7.38 (m, 3 H), 7.37-7.28 (m, 3 H), 7.16-7.10 (dt, J=1, 6 Hz, 1 H), 6.76 (d, J=8 Hz, 1 H), 5.45 (t, J=7 Hz, 1 H, CH), 3.59 (d, J=7 Hz, 2 H), 2.98 (s, 3 H); MS (EI): [M+], 643.6 (20%), 644.4 (50%), 645.5 (100%) 647.7 (30%); Anal. Calc. for C32H22Br2O3S: C, 59.46, H, 3.43, N, 0.00. Found: C, 59.34, H, 3.24, N, 0.04.

Sources & evidence

ORD record
ord-07d293ae3975415cac95c1be54b619b1
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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