Benzyl chloroformate → HCID 67195158, compound

HRID 1841932Notes

Reaction equation

HRID 1841932 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(N(C(C)C)CC)(C)C>C1COCC1.C(OCC)(=O)C>[CH2:5]([O:4][C:2]([N:28]1[CH2:29][CH2:30][CH:25]([NH:24][S:21]([C:18]2[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:20][CH:19]=2)(=[O:23])=[O:22])[CH2:26][CH2:27]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 16781088HCID 16781088, compound

Product 1

HCID 67195158HCID 67195158, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl chloroformate (0.7 ml, 4.9 mmol) was added drop wise to a cool (0° C.) solution of 4-nitro-N-piperidin-4-yl-benzenesulfonamide (1.4 g, 4.9 mmol) and diisopropylethylamine (1.6 ml, 9.8 mmol) in THF (10 ml). The resulting mixture was warmed to room temperature and stirred under a nitrogen atmosphere for 18 hours. After this time, the mixture was diluted with ethyl acetate (50 ml), washed with water (50 ml), the organic layer was separated and dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was purified by flash column chromatography (elution: 50% heptane, 50% ethyl acetate) to give the title compound (0.98 g, 48% yield) as a white solid. Tr=2.04 min m/z (ES+) (M+H+) 420.

Workup

  1. washwashed with water (50 ml)
  2. customthe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe resulting residue was purified by flash column chromatography (elution: 50% heptane, 50% ethyl acetate)

Sources & evidence

ORD record
ord-01b77dd3c262444e8c17b53ff4d5a824
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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