Pyridine → HCID 70983147, compound

HRID 1506756Notes

Reaction equation

HRID 1506756 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].N1C=CC=CC=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[CH2:1]([N:3]([CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[S:26]([CH3:25])(=[O:28])=[O:27])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 70982982HCID 70982982, compound

Product 1

HCID 70983147HCID 70983147, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of benzyl 4-(ethylamino)butylcarbamate (Step 1, 250 mg, 1.00 mmol) in dichloromethane was added pyridine (145 mg, 1.8 mmol) and then methanesulfonyl chloride (137 mg, 1.20 mmol) at 0° C. The reaction was stirred overnight and diluted with dichloromethane. The phases were separated, and the organic phase was washed with hydrochloride solution (1 N), saturated sodium bicarbonate and saline. The separated organic layer was concentrated and purified by Biotage column chromatography to give benzyl 4-(N-ethylmethylsulfonamido)butylcarbamate (231 mg).

Workup

  1. customat 0° C
  2. customThe phases were separated
  3. washthe organic phase was washed with hydrochloride solution (1 N), saturated sodium bicarbonate and saline
  4. concentrationThe separated organic layer was concentrated
  5. custompurified by Biotage column chromatography

Sources & evidence

ORD record
ord-0bc3ab86cc8044088d0810536854aa5c
Source dataset
uspto-grants-2015_12
Patent number
US09221760B2

Reaction notes

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