(S)-methyl 2-hydroxy-3-phenylpropanoate → HCID 54172641, compound

HRID 1873179Notes

Reaction equation

[CH3:1][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]([CH3:26])[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]>>[CH3:1][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]([CH3:26])[C:3]=1[O:27][C@H:29]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30]([OH:32])=[O:31]

Participants

Reactant 2

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

HCID 15481244HCID 15481244, compound

Product 1

HCID 54172641HCID 54172641, compound

Procedure

Prepared from of 2,6-dimethyl-4-(6-methyl-benzo[b]naphtho [2,3-d]thiophen-11-yl)-phenol (Example 25) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: NMR (DMSO-d6); δ13.0 (broad band, 1 H), 8.18 (d, J=8 Hz, 1 H), 7.91(d, J=8 Hz, 1 H), 7.61 - 7.53 (m, 2 H), 7.43 (ddd, J=8, 7, 1 Hz, 1 H), 7.45 - 7.28(m, 5 H), 7.25 - 7.21 m, 1 H), 7.01 (ddd, J=8, 7, 1 Hz, 1 H), 6.95 (d, J=5 Hz, 2 H), 6.53 (d, J=8Hz, 1 H), 4.75 (t, J=7 Hz, 1 H), 3.32 - 3.24 (m, 2 H), 2.87 (s, 3 H), 2.56 (s, 3 H), 2.18 (s, 3 H): MS(EI): [M+] 516; Anal. Calc. for C34H28O3S: C, 79.04, H, 5.46, N, 0.00. Found: C, 79.13, H, 5.41, N, 0.11.

Sources & evidence

ORD record: ord-9d7e37f044174a5b92be1f66d10e5326
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06110962

Reaction notes

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