Sulfamide → (R,R)-(+)-N,N'-Bis(alpha-methylbenzyl)sulfamide

HRID 278520Notes

Reaction equation

HRID 278520 reaction equation
CO[C:3](=O)[C@H:4]([CH:18]([CH3:20])[CH3:19])[NH:5][S:6]([NH:9][C@H:10]([C:14](OC)=O)[CH:11]([CH3:13])[CH3:12])(=[O:8])=[O:7].S(N)(N)(=O)=O>CCN(CC)CC>[S:6]([NH:9][C@@H:10]([C:11]1[CH:13]=[CH:14][CH:10]=[CH:11][CH:12]=1)[CH3:14])([NH:5][C@@H:4]([C:18]1[CH:20]=[CH:18][CH:4]=[CH:3][CH:19]=1)[CH3:3])(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 12051191HCID 12051191, compound

Product 1

HCID 688088(R,R)-(+)-N,N'-Bis(alpha-methylbenzyl)sulfamideYield 63%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a procedure similar to the preparation of sulfamide (8b), (R)-phenethylamine (471 mg, 501 μL, 3.84mmol) was subjected to sulfamide formation conditions (SO2Cl2, Et3N, CH2Cl20° C.-RT, 8 h). Flash chromatography (SiO2, Hexanes/EtOAc) yielded 356 mg (63%) of sulfamide (8e) as a white solid. mp=96-97° C.; TLC Rf=0.37 (3:1 Hexanes/EtOAc); [α]25D=−31.2 (c=1.02, CHCl3); 1H NMR (CDCl3, 400 MHZ) δ7.27-7.21 (m, 6H), 7.17-7.14 (m, 4H), 4.74 (s, 2H), 4.43 (dq, J=12.2. 6.2 Hz, 2H), 1.46 (d, J=6.8Hz, 6H); 13C NMR (CDCl3, 100 MHZ) δ142.7, 128.6, 127.5, 126.1, 53.7, 23.6; FTIR(neat) 3312,3032,2992,2944,1603,1493,1454,1381,1320,1149,751,701 cm−1; HRMS (M+H)+ calculated for C16H21N2O2S 305.1324, found 305.1322.

Sources & evidence

ORD record
ord-92d3ab27a63f43de86ab12b0414fa5f0
Source dataset
uspto-grants-2002_03
Patent number
US06359129B1

Reaction notes

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