HCID 388023, compound → HCID 388024, compound

HRID 1250217Notes

Reaction equation

HRID 1250217 reaction equation
[C:1]([C:4]1[S:8][C:7]2[C:9](=[O:17])[C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:15](=[O:16])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[S:8][C:7]2[C:9](=[O:17])[C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:15](=[O:16])[C:6]=2[CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 388023HCID 388023, compoundHCID 4311764Sodium borohydride

Product 1

HCID 388024HCID 388024, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 9 (3.0 g, 11.2 mmol) in MeOH (200 mL) was added NaBH4 (1.5 g, 39.7 mmol) and stirring continued for 2 h. After acidification with dilute HCl, the solution was extracted with CHCl3. The organic fraction was washed with water, dried, and condensed. The residue was purified by column chromatography (silica gel, CHCl3) to give 10 as a yellow solid (mp 166-168° C.) in a 93% yield. IR (KBr) 1650, 1680 (C═O), 3200-3600 (OH) cm−1; 1H NMR (DMSO-d6) δ 1.48 (d, J=6.3 Hz, 3H, CH3), 5.02-5.07 (m, 1H, CH), 6.10 (d, J=4.8 Hz, 1H, OH), 7.45 (s, 1H, H-3), 7.62 (d, J=5.1 Hz, 1H, H-7), 8.15 (d, J=5.1 Hz, 1H, H-6); 13C NMR (DMSO-d6): δ 25.3 (C-2-CH3), 64.6 (C-2-CH), 120.7 (C-3), 126.1 (C-7), 135.5 (C-6), 163.0 (C-2), 174.0, 174.4 (C-4, C-8); MS m/z 264 (M+); Anal. (Cl2H8O3S C, H.

Workup

  1. extractionAfter acidification with dilute HCl, the solution was extracted with CHCl3
  2. washThe organic fraction was washed with water
  3. customdried
  4. customcondensed
  5. customThe residue was purified by column chromatography (silica gel, CHCl3)

Sources & evidence

ORD record
ord-b355ac2206b443a98eadd433cb494b19
Source dataset
uspto-grants-2002_01
Patent number
US06337346B1

Reaction notes

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