methyl (S)-lactate → HCID 70196870, compound

HRID 1873181Notes

Reaction equation

HRID 1873181 reaction equation
[Br:1][C:2]1[C:14]2[S:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10]=2[C:9]([C:19]2[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[C:22]([OH:28])=[C:21]([CH:29]([CH3:31])[CH3:30])[CH:20]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[C:32]([O:37]C)(=[O:36])[C@H:33]([CH3:35])O>>[Br:1][C:2]1[C:14]2[S:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10]=2[C:9]([C:19]2[CH:24]=[C:23]([CH:25]([CH3:26])[CH3:27])[C:22]([O:28][C@H:33]([CH3:35])[C:32]([OH:37])=[O:36])=[C:21]([CH:29]([CH3:31])[CH3:30])[CH:20]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2

Participants

3

Reactant 2

HCID 94386methyl (S)-lactateHCID 15481257HCID 15481257, compound

Product 1

HCID 70196870HCID 70196870, compound

Procedure

Prepared from of 4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-2,6-diisopropyl-phenol (Example 40) and commercially available (S)-lactic acid, methyl ester. White solid: mp: 214-215° C.; NMR (CDCl3); δ8.37 (ddd, J=8, 1, 1, 1H), 7.80 (d, J=8 Hz, 1 H), 7.70 (ddd, J=8, 1, 1 Hz, 1 H), 7.66 (ddd, J=8, 8, 1, 1 H), 7.48 (ddd, J=8, 8, 1 Hz, 1 H), 7.37 (ddd, J=8, 8, 1 Hz, 1 H), 7.18 (s, 2 H), 7.01 (ddd, J=8, 8, 1 Hz, 1 H), 6.53 (d, J=8 Hz, 1 H), 4.75 (q, J=7 Hz, 1 H), 3.47 (septuplet, J=7 Hz, 1 H), 3.41 (septuplet, J=7 Hz, 1 H), 1.71 (d, J=7 Hz, 3 H), 1.25 (d, J=7 Hz, 6 H), 1.20 (d, J =7 Hz, 3 H), 1.19 (d, J=7 Hz, 3 H); MS (EI): 560 (90%), 562 (100); Anal. Calc. for C31H29BrO3S: C, 66.31, H, 5.21, N, 0.00. Found: C, 65.90, H, 5.18, N, 0.02.

Sources & evidence

ORD record
ord-5763fb51562b4f19b073bd9fa884fdba
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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