Acetone → Methyl 2-[(tert-butylamino)sulfonyl]-6-(isopropylamino)benzoate

HRID 2218943Notes

Reaction equation

HRID 2218943 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([CH3:6])=O.[NH2:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([NH:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])=[O:19])[C:9]=1[C:10]([O:12][CH3:13])=[O:11].N>C(O)(=O)C>[C:22]([NH:21][S:18]([C:14]1[CH:15]=[CH:16][CH:17]=[C:8]([NH:7][CH:4]([CH3:6])[CH3:3])[C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:20])=[O:19])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 180AcetoneHCID 222AmmoniaHCID 4311764Sodium borohydrideHCID 22024119HCID 22024119, compound

Product 1

HCID 22024116Methyl 2-[(tert-butylamino)sulfonyl]-6-(isopropylamino)benzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

At a temperature of 5-10° C., 925 mg (24.4 mmol) of sodium borohydride are stirred into 14 ml of acetic acid. After 1 h, this mixture is admixed first with 1.42 g (24.4 mmol) of acetone and then with 700 mg (2.44 mmol) of methyl 2-amino-6-[(tert-butylamino)sulfonyl]benzoate and stirred at 5-10° C. for 2.5 h. For work-up, the reaction mixture is poured into ice-water, neutralized with aqueous ammonia solution and extracted with dichloromethane. The organic phase is concentrated and the residue that remains is triturated with diisopropyl ether. After filtration with suction and drying, 700 mg (89% of theory) of methyl 2-[(tert-butylamino)sulfonyl]-6-(isopropylamino)benzoate remain as a white solid of m.p. 110-112° C.

Workup

  1. extractionextracted with dichloromethane
  2. concentrationThe organic phase is concentrated
  3. customthe residue that remains is triturated with diisopropyl ether
  4. filtrationAfter filtration with suction
  5. customdrying

Sources & evidence

ORD record
ord-3fe6dba220154218bd805522c50fdbb2
Source dataset
uspto-grants-2008_08
Patent number
US07414011B2

Reaction notes

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