4-Methylbenzenethiol → HCID 22005006, compound

HRID 324894Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[CH:9]([C:12]1[C:13]([CH2:32][OH:33])=[C:14]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:15]([CH2:21]C(O)=O)=[C:16]([CH:18]([CH3:20])[CH3:19])[CH:17]=1)([CH3:11])[CH3:10].[CH2:34](Cl)Cl.CCCCCC>>[CH:18]([C:16]1[C:15]([CH2:21][S:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[C:14]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:13]([CH:32]([OH:33])[CH3:34])=[C:12]([CH:9]([CH3:11])[CH3:10])[CH:17]=1)([CH3:20])[CH3:19]

Participants

Reactant 3

HCID 78114-Methylbenzenethiol

HCID 21226440Methylenechloride Hexane

HCID 22004884HCID 22004884, compound

Product 1

HCID 22005006HCID 22005006, compound

Procedure

The title compound was prepared from p-thiocresol and 3,5-diisopropyl-2-hydroxymethyl-6-carboxymethyl-4′-fluoro-1,1′-biphenyl (Example 244, Step D), according to the procedures described in Example 47, Steps B and C, followed by the procedures described in Example 244, Steps I-K. Rf=0.36 (70% CH2Cl2/hexane); 1H NMR (300 MHz, CDCl3): δ 7.40 (s, 1H), 7.28 (m, 2H), 7.11 (m, 6H), 4.76 (dq, J=1.8, 7 Hz, 1H), 3.92 (septet, J=6.6 Hz, 1H), 3.78 (s, 2H), 3.26 (septet, J=6.6 Hz, 1H), 2.36 (s, 3H), 1.66 (s, 1H), 1.40 (d, J=6.6 Hz, 3H), 1.28 (m, 12H); FAB-MS calcd for (C28H33FOS) 436, found 436 (M+); Anal. Calcd for C29H35FOS: C, 77.02; H, 7.62; S, 7.34; F, 4.35. Found: C, 76.90; H, 7.77; S, 7.30; F, 4.37; [α]22=+32.2.

Sources & evidence

ORD record: ord-044bd9cae39d4e97acf78ececd5689b9
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218431B1

Reaction notes

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