HCID 12074224, compound → HCID 12074225, compound

HRID 1356545Notes

Reaction equation

HRID 1356545 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[CH:8]=[CH:9][C:10]=1[S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])(=O)[CH3:2]>C1COCC1>[CH2:1]([NH:4][C:5]1[CH:6]=[C:7]([N:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:24][CH2:25]2)[CH:8]=[CH:9][C:10]=1[S:11]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:12])[CH3:2]

Participants

3

Reactant 1

HCID 12074224HCID 12074224, compound

Product 1

HCID 12074225HCID 12074225, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl 4-[3-(acetylamino)-4-(phenylsulfonyl)phenyl]-1-piperazinecarboxylate (0.44 g, 0.96 mmol) in 7 nL of dry THF is added borane-methyl sulfide complex (0.28 mL, 2.8 mmol, 10.0 M). The mixture is stirred at rt overnight. The reaction is quenched upon dropwise addition of 10% HCl. Water (3.0 mL) and KOH (2.0 g) are added, the mixture heated at reflux for 6 h. At that time methanol (2 mL) is added and the mixture stirred at reflux overnight. After cooling to rt, the organics are removed under reduced pressure, the aqueous layer is saturated with NaCl, and extracted with CH2Cl2 (3×10 mL). The combined organic layers are dried over MgSO4, filtratered, and concentrated to give the crude product. Purification by column chromatography (15% EtOAc/hexane) gave 0.18 g (43%) of the pure title compound as an oil.

Workup

  1. additionis added borane-methyl sulfide complex (0.28 mL, 2.8 mmol, 10.0 M)
  2. customThe reaction is quenched upon dropwise addition of 10% HCl
  3. additionWater (3.0 mL) and KOH (2.0 g) are added
  4. temperaturethe mixture heated
  5. temperatureat reflux for 6 h
  6. additionAt that time methanol (2 mL) is added
  7. stirringthe mixture stirred
  8. temperatureat reflux overnight
  9. temperatureAfter cooling to rt
  10. customthe organics are removed under reduced pressure
  11. extractionextracted with CH2Cl2 (3×10 mL)
  12. dry with materialThe combined organic layers are dried over MgSO4
  13. concentrationconcentrated
  14. customto give the crude product
  15. customPurification by column chromatography (15% EtOAc/hexane)

Sources & evidence

ORD record
ord-98e39f678775444387007bd022494e43
Source dataset
uspto-grants-2003_07
Patent number
US06586592B2

Reaction notes

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