Water → Tert-butyl 4-chloro-2-nitrophenyl(3-(methylsulfonyl)propyl)carbamate

HRID 1500841Notes

Reaction equation

HRID 1500841 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH2:32][CH2:33][CH2:34][S:35]([CH3:38])(=[O:37])=[O:36])(=O)=O)=CC=1.O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:32][CH2:33][CH2:34][S:35]([CH3:38])(=[O:37])=[O:36])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 22732325(3-(Methylsulfonyl)propyl 4-methylbenzenesulfonateHCID 539801451,1-Dimethylethyl N-(4-chloro-2-nitrophenyl)carbamate

Product 1

HCID 89923963Tert-butyl 4-chloro-2-nitrophenyl(3-(methylsulfonyl)propyl)carbamateYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-Chloro-2-nitro-phenyl)-(3-methanesulfonyl-propyl)-carbamic acid tert-butyl ester was prepared according to Scheme 1. To a solution of tert-butyl 4-chloro-2-nitrophenylcarbamate (580 mg, 2.1 mmol) in DMF (5 mL) was added NaH (170 mg, 4.3 mmol, 60 wt %). The mixture was stirred for 30 min at RT, then 3-(methylsulfonyl)propyl 4-methylbenzenesulfonate (0.75 g, 2.56 mmol) was added. The solution was heated to 50° C. and stirred for overnight. After cooled to RT, H2O (30 mL) was added and the solution was extracted with DCM (40 mL×3). The organic layer was dried over anhydrous and concentrated. The residue was purified by prep-TLC (DCM) to give tert-butyl 4-chloro-2-nitrophenyl(3-(methylsulfonyl)propyl)carbamate (360 mg, yield: 69%) as pale oil. MS obsd. (ESI+) [(M+H)+]: 393.0.

Workup

  1. custom(4-Chloro-2-nitro-phenyl)-(3-methanesulfonyl-propyl)-carbamic acid tert-butyl ester was prepared
  2. temperatureThe solution was heated to 50° C.
  3. stirringstirred for overnight
  4. temperatureAfter cooled to RT
  5. extractionthe solution was extracted with DCM (40 mL×3)
  6. customThe organic layer was dried over anhydrous and
  7. concentrationconcentrated
  8. customThe residue was purified by prep-TLC (DCM)

Sources & evidence

ORD record
ord-9906c48ddc46449ab869ef4543614d00
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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