Allyl bromide → HCID 18710119, compound

HRID 278522Notes

Reaction equation

HRID 278522 reaction equation
CO[C:3](=O)[C@H:4]([CH:24]([CH3:26])[CH3:25])[N:5]([CH2:21][CH:22]=[CH2:23])[S:6]([N:9]([CH2:18][CH:19]=[CH2:20])[C@H:10]([C:14](OC)=O)[CH:11]([CH3:13])[CH3:12])(=[O:8])=[O:7].S(N[C@@H](C1C=CC=CC=1)C)(N[C@@H:32]([C:34]1C=CC=CC=1)[CH3:33])(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH2:55](Br)[CH:56]=[CH2:57]>CC#N>[CH2:18]([N:9]([C@@H:10]([C:11]1[CH:13]=[CH:57][CH:56]=[CH:55][CH:12]=1)[CH3:14])[S:6]([N:5]([CH2:21][CH:22]=[CH2:23])[C@@H:4]([C:24]1[CH:26]=[CH:34][CH:32]=[CH:33][CH:25]=1)[CH3:3])(=[O:8])=[O:7])[CH:19]=[CH2:20]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 688088(R,R)-(+)-N,N'-Bis(alpha-methylbenzyl)sulfamideHCID 12051192HCID 12051192, compound

Product 1

HCID 18710119HCID 18710119, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a procedure similar to that used for the preparation of allylated sulfamide (9b), sulfamide (8e) (250 mg, 0.821 mmol) was subjected standard allylation procedures (K2CO3, allyl bromide, CH3CN 70° C., 24 hours). Flash chromatography (SiO2, Hexanes/EtOAc) yielded 313 mg (99%) of sulfamide (9e) as a clear oil. TLC Rf=0.59 (10:1 Hexanes/EtOAc); [α]25D=+77.5 (c=1.00, CHCl3); 1H NMR (CDCl3, 400 MHz) 7.46 (d, J=7.4 Hz, 4H), 7.39-7.35 (m, 4H), 7.32-7.30 (m, 2H), 5.79 (dddd, J=15.7, 9.7, 7.1, 5.8 Hz, 2H), 5.19 (q, J=7.1 Hz, 2H), 5.03 (dd, J=6.1, 1.3 Hz, 2H), 5.01-4.99 (m, 2H), 3.77 (dd with small allylic coupling, J=16.3, 5.8 Hz, 2H), 3.55 (dd, J=16.3, 7.2 Hz, 2H), 1.67 (d, J=7.1 Hz, 6H); 13C NMR (CDCl3, 100 MHz) 140.1, 135.9, 128.2, 127.9, 127.5, 116.9, 56.5, 47.3, 17.9; FTIR(neat) 3064, 3030, 2980, 2937, 1640, 1603, 1496, 1452, 1378, 1323, 1161, 784, 699 cm−1; HRMS (M+H)+ calculated for C22H29N2O2S 385.1950, found 385.1958.

Sources & evidence

ORD record
ord-f3702ececb9c4ed196a95980da13e46e
Source dataset
uspto-grants-2002_03
Patent number
US06359129B1

Reaction notes

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