4-Toluenesulfonyl chloride → HCID 86662381, compound

HRID 578621Notes

Reaction equation

HRID 578621 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1.C(N(CC)CC)C.[CH3:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>C(Cl)Cl>[CH3:29][C:30]1[CH:35]=[CH:34][C:33]([S:36]([O:1][CH2:2][CH2:3][CH:4]([NH:14][C:15]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:21])[C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)(=[O:38])=[O:37])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 19104047HCID 19104047, compound

Product 1

HCID 86662381HCID 86662381, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [3-hydroxy-1-(3-nitrophenyl)propyl]carbamate (4.00 g; 13.50 mmol; 1.00 eq.) in anhydrous DCM (15 mL) and N,N-diethylethanamine (2.82 ml; 20.25 mmol; 1.50 eq.) at 0° C. was added dropwise 4-methylbenzenesulfonyl chloride (3.09 g; 16.20 mmol; 1.20 eq.). The mixture was stirred at room temperature for 15 h. After workup, the crude product was purified by flash chromatography on silica gel (EtOAc:Hex from 10:90 to 20:80) to provide 5.5 g of the 3-[(tert-butoxycarbonyl)amino]-3-(3-nitrophenyl)propyl 4-methylbenzenesulfonate.

Workup

  1. customAfter workup, the crude product was purified by flash chromatography on silica gel (EtOAc:Hex from 10:90 to 20:80)

Sources & evidence

ORD record
ord-50e1c943ead24f9c904aa7c3f97c75f0
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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