Isopropyl Acetate → HCID 66770541, compound

HRID 1697684Notes

Reaction equation

HRID 1697684 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=O.[CH3:8][S:9]([C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15])(=[O:11])=[O:10].C([BH3-])#N.[Na+].C(OC(C)=O)(C)C>C1(C)C=CC=CC=1.CO.C(O)(=O)C>[CH2:6]([O:5][C:1](=[O:4])[CH2:2][NH:15][C:14]1[CH:16]=[CH:17][CH:18]=[C:12]([S:9]([CH3:8])(=[O:11])=[O:10])[CH:13]=1)[CH3:7]

Participants

8

Reactant 4

HCID 7915Isopropyl AcetateHCID 70211Ethyl oxoacetateHCID 4280293-(Methylsulphonyl)anilineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 66770541HCID 66770541, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A 0.5 M solution of ethyl glyoxalate in toluene (0.95 ml, 5 mmol; CAS Reg. No. 924-44-7) and acetic acid (0.4 ml) were added to an ice cold solution of 3-(methylsulfonyl)aniline (500 mg, 2 mmol; CAS Reg. No. 5470-49-5) in methanol (6.3 ml) under an argon atmosphere. Sodium cyanoborohydride (356 mg, 5 mmol) was added in 3 portions within 10 min. The reaction mixture was stirred for 45 min at 0° C. and then at ambient temperature over night. The reaction mixture was poured onto ice water (100 ml). iPrOAc (100 ml) was added and the layers were separated. The aqueous layer was extracted one more time with iPrOAc (100 ml). The combined extracts were washed two times with ice water/brine 1/1 and dried over sodium sulfate. After filtering the solvent was removed under reduced pressure to give the crude product as yellow foam which was purified by column chromatography (silica gel, iPrOAc/n-heptane) to obtain the title compound (350 mg, 1 mmol; 56%) as white solid. MS (ESI): m/z=258.2 [M+H]+.

Workup

  1. waitat ambient temperature over night
  2. additionThe reaction mixture was poured onto ice water (100 ml)
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted one more time with iPrOAc (100 ml)
  5. washThe combined extracts were washed two times with ice water/brine 1/1
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtering the solvent
  8. customwas removed under reduced pressure
  9. customto give the crude product as yellow foam which
  10. customwas purified by column chromatography (silica gel, iPrOAc/n-heptane)

Sources & evidence

ORD record
ord-32b321cd00f7401facebef980a148aa7
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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