Acetonitrile → HCID 12051192, compound

HRID 278521Notes

Reaction equation

HRID 278521 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[CH3:11][O:12][C:13](=[O:31])[C@H:14]([CH:28]([CH3:30])[CH3:29])[NH:15][S:16]([NH:19][C@H:20]([C:24]([O:26][CH3:27])=[O:25])[CH:21]([CH3:23])[CH3:22])(=[O:18])=[O:17].[CH3:32][C:33]#N>>[CH3:11][O:12][C:13](=[O:31])[C@H:14]([CH:28]([CH3:30])[CH3:29])[N:15]([CH2:1][CH:33]=[CH2:32])[S:16]([N:19]([CH2:7][CH:8]=[CH2:9])[C@H:20]([C:24]([O:26][CH3:27])=[O:25])[CH:21]([CH3:23])[CH3:22])(=[O:17])=[O:18]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 12051191HCID 12051191, compound

Product 1

HCID 12051192HCID 12051192, compoundYield 98.7%

Conditions

Temperature
70 °C

Procedure

K2CO3(1.06 g, 7.70 mmol) and allyl bromide were added to a stirring solution of sulfamide (8b ) (500 mg, 1.54 mmol) in CH3CN (35 mL) in a 100 mL round-bottom flask (1.12 g, 9.24 mmol). The flask was fitted with a condenser, and the mixture was heated to 70° C. for 14 hours. The resulting yellow orange mixture was filtered by suction, and the solvent was removed under reduced pressure to give a yellow oil. Flash Chromatography (SiO2, 10:1 Hexanes/EtOAc) afforded 619 mg (98.7%) of sulfamide (9b) as a clear oil. TLC Rf=0.31 (10:1 Hexanes/EtOAc); [α]25D=−89.3 (c=1.00, CHCl3); 1H NMR (CDCl3, 400 MHZ) 5.92 (dddd, J=15.9, 10.2, 7.5, 5.7 Hz, 2H), 5.14 (dd, J=16, 1.3 Hz, 2H), 5.05 (dd, J=10.2, 1.2 Hz, 2H), 3.99-3.90 (m, 6H), 3.68 (s, 6H), 2.16-2.08 (m, 2H), 0.97 (d, J=6.7 Hz, 6H), 0.86 (d, J=6.6, 6H); 13C NMR (CDCl3, 100MHZ) 171.6, 135.2, 117.3, 66.3, 51.5, 47.7,28.4, 19.6, 19.5; FTIR (neat) 3080, 1745, 1640, 1436, 1351, 1137 cm−1; HRMS (M+H)+ calculated for C18H33N2O6S 405.2059, found 405.2031.

Workup

  1. customThe flask was fitted with a condenser
  2. filtrationThe resulting yellow orange mixture was filtered by suction
  3. customthe solvent was removed under reduced pressure
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-3b31eb99e4c148f7b0c7d79846c81087
Source dataset
uspto-grants-2002_03
Patent number
US06359129B1

Reaction notes

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