Citric Acid → HCID 86753326, compound

HRID 356499Notes

Reaction equation

HRID 356499 reaction equation
CO[C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:7]([S:14]C(=O)N(C)C)=[CH:6][C:5]=1C.[CH3:22]C(C[AlH]CC(C)C)C.C(Cl)Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1>[C:10]([C:8]1([CH3:22])[CH:9]=[C:4]([CH2:3][OH:21])[CH:5]=[CH:6][CH:7]1[SH:14])([CH3:11])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 10518962HCID 10518962, compoundHCID 131720939HCID 131720939, compound

Product 1

HCID 86753326HCID 86753326, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 12.2 g (39.4 mmol) of 5-tert-butyl-4-dimethylcarbamoylsulfanyl-2-methyl-benzoic acid methyl ester (prepared in Example DDD) in toluene (140 mL) cooled to -78° C. under nitrogen was added 1.0M DIBAL/CH2Cl2 (236.6 mL), dropwise over a 2.5 hour period. The reaction mixture was stirred an additional 30 minutes at -78° C. following addition, then at 0° C. for 1 hour. Saturated aqueous citric acid solution (approximately 600 mL) was added very slowly and carefully. The mixture was then extracted twice with EtOAc; the organic phases were combined, washed with brine, dried (MgSO4), filtered and concentrated to give the title compound. 1H NMR (CDCl3) δ 1.47 (s, 9 H), 2.27 (s, 3 H), 3.57 (s, 1 H), 4.63 (s, 2 H), 7.06 (s, 1 H), 7.32 (s, 1 H).

Workup

  1. customcooled to -78° C. under nitrogen
  2. additionaddition
  3. waitat 0° C. for 1 hour
  4. extractionThe mixture was then extracted twice with EtOAc
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-153edd0048e947a9aacd29daf0c99394
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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