HCID 388024, compound → HCID 388026, compound

HRID 1250219Notes

Reaction equation

HRID 1250219 reaction equation
[C:1]([C:4]1[S:8][C:7]2[C:9](=[O:20])[C:10]3[C:14]([C:15](=[O:17])[CH3:16])=[CH:13][S:12][C:11]=3[C:18](=[O:19])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].OC(C1SC2C(=O)C3C=CSC=3C(=O)C=2C=1)C>C(Cl)(Cl)Cl.CO>[OH:3][CH:1]([C:4]1[S:8][C:7]2[C:9](=[O:20])[C:10]3[C:14]([CH:15]([OH:17])[CH3:16])=[CH:13][S:12][C:11]=3[C:18](=[O:19])[C:6]=2[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 388024HCID 388024, compoundHCID 4311764Sodium borohydrideHCID 10780817HCID 10780817, compound

Product 1

HCID 388026HCID 388026, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Compound 13 was reduced with NaBH4 as in the preparation of 10. Column chromatography on silica gel eluting with CHCl3:MeOH (100:1) gave 14 as a yellow solid (mp 218-219° C.) in a 90% yield. IR (KBr) 1650, 1670 (C═O), 3100-3500 (OH) cm−1; 1H NMR (DMSO-d6) δ 1.36 (d, J=6.0 Hz, 3H, C-7-CH3), 1.48 (d, J=6.0 Hz, 3H, C-2-CH3), 5.05 (s, 1H, C-2-OH), 5.33 (s, 1H, C-7-OH), 5.52 (m, 1H, C-7-CH), 6.17 (m, 1H, C-2-CH), 7.41 (s, 1H, H-3), 7.97 (s, 1H, H-6); 13C NMR (DMSO-d6) δ 24.8 (C-7-CH3), 25.5 (C-2-CH3), 64.1 (C-7-CH), 64.9 (C-2-CH), 120.7 (C-3), 130.1 (C-6), 174.7 (C-4), 175.3 (C-8); MS m/z 308 (M+); Anal. (C14H12O4S2) C, H.

Sources & evidence

ORD record
ord-267bf1b4a20e4476a558c613cc9fa061
Source dataset
uspto-grants-2002_01
Patent number
US06337346B1

Reaction notes

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