4-Toluenesulfonyl chloride → Carbamic acid, N-[1-[[[(4-methylphenyl)sulfonyl]oxy]methyl]cyclopropyl]-, 1,1-dimethylethyl ester

HRID 1504800Notes

Reaction equation

HRID 1504800 reaction equation
[OH:1][CH2:2][C:3]1([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5][CH2:4]1.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:1][CH2:2][C:3]2([NH:6][C:7]([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:13])[CH2:4][CH2:5]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 11286907tert-butyl N-(1-(hydroxymethyl)cyclopropyl)carbamate

Product 1

HCID 86731683Carbamic acid, N-[1-[[[(4-methylphenyl)sulfonyl]oxy]methyl]cyclopropyl]-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-(hydroxymethyl)cyclopropylcarbamate (290 g, 1.55 mol) in DCM (2900 mL) was added DMAP (227 g, 1.86 mol) followed by 4-methylbenzene-1-sulfonyl chloride (323 g, 1.69 mol) in several batches at 10° C. After 2 hours, the reaction mixture was washed with water (2×1000 mL), dried over sodium sulfate, and concentrated under reduced pressure to afford {1-[(tert-butoxycarbonyl)amino]cyclopropyl}methyl 4-methylbenzenesulfonate. The material was used without further purification.

Workup

  1. washthe reaction mixture was washed with water (2×1000 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-773137f16a874097a066f8558251600d
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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