Methanesulfonic Acid → HCID 71183848, compound

HRID 1422589Notes

Reaction equation

HRID 1422589 reaction equation
C([NH:5][C:6]1[S:13][CH2:12][CH2:11][CH:10]2[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=3)([CH2:9]2)[N:7]=1)(C)(C)C.FC(F)(F)C(O)=O.CS(O)(=O)=O.C([O-])(O)=O.[Na+]>>[N+:20]([C:16]1[CH:15]=[C:14]([C:8]23[CH2:9][CH:10]2[CH2:11][CH2:12][S:13][C:6]([NH2:5])=[N:7]3)[CH:19]=[CH:18][CH:17]=1)([O-:22])=[O:21]

Participants

5

Reactant 4

HCID 6395Methanesulfonic AcidHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 71183711HCID 71183711, compound

Product 1

HCID 71183848HCID 71183848, compound

Conditions

Temperature
23 °C

Procedure

To a solution of (1SR,7SR)—N-tert-butyl-1-(3-nitrophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-amine (intermediate A4c) (990 mg, 3.1 mmol, Eq: 1.00) in trifluoroacetic acid (25.4 g, 17.2 ml, 223 mmol, Eq: 72) was added methanesulfonic acid (2.98 g, 2.01 ml, 31.0 mmol, Eq: 10) and the mixture was stirred at 23° C. for 20 hours. The light brown solution was poured cautiously into sat NaHCO3 solution, extracted with ethyl acetate, washed the organic layer with brine and dried over Na2SO4. Removal of the solvent in vacuum left a light brown oil (910 mg, ca. 90% purity; 100%). The crude product either chromatographed on amine-coated silica gel using n-heptane and ethyl acetate or was used in the next step without further purification. MS (ISP): m/z=264.1 [(M+H)+].

Workup

  1. additionThe light brown solution was poured cautiously
  2. extractionextracted with ethyl acetate
  3. washwashed the organic layer with brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent in vacuum
  6. waitleft a light brown oil (910 mg, ca. 90% purity; 100%)
  7. customThe crude product either chromatographed on amine-coated silica gel
  8. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-c0aa588cf0df4656b5a7adf9a41d04a1
Source dataset
uspto-grants-2015_01
Patent number
US08927535B2

Reaction notes

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