Triethylamine → HCID 89590946, compound

HRID 522355Notes

Reaction equation

HRID 522355 reaction equation
[CH:1]1([S:4]([NH2:7])(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:19]([O:18][C:16](=[O:17])[NH:7][S:4]([CH:1]1[CH2:3][CH2:2]1)(=[O:6])=[O:5])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 15765418Cyclopropanesulfonamide

Product 1

HCID 89590946HCID 89590946, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of cyclopropanesulfonamide (6.51 g, triethylamine (40 mL) and DMAP (0.656 g) in DCM (150 mL) was slowly added benzyl chloroformate (12 mL). The mixture was stirred at room temperature for 18 hours. The mixture was washed with 1 N HCl. The aqueous layer (pH 1) was extracted with EtOAc (×2). The combined organics were washed with brine, dried over anhydrous MgSO4 and concentrated. The resulting residue was purified by flash chromatography (ISCO, 0-10% methanol in dichloromethane) to afford the desired product (7.8 g). 1H NMR (400 MHz, CDCl3): δ (ppm) 7.56-7.44 (m, 1H), 7.38 (s, 5H), 5.22 (s, 2H), 2.92-2.84 (m, 1H), 1.40-1.35 (m, 2H), 1.12-1.06 (m, 2H).

Workup

  1. washThe mixture was washed with 1 N HCl
  2. extractionThe aqueous layer (pH 1) was extracted with EtOAc (×2)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash chromatography (ISCO, 0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-79b52137fd644935ae221bdfb82d1408
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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