Acetone → HCID 131719652, compound

HRID 1900888Notes

Reaction equation

HRID 1900888 reaction equation
[C:1]([C:4]1[CH:37]=[CH:36][C:7]([C:8]([NH:10][C:11](=[O:35])[NH:12][C:13]2[CH:27]=[CH:26][C:16]([O:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:15]([O:28][CH2:29][O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:14]=2)=[O:9])=[CH:6][CH:5]=1)(=S)[NH2:2].IC.CC(C)=O.C([O-])(=O)C.[NH4+:48]>ClCCl.CO>[C:19]([OH:21])(=[O:20])[CH3:18].[C:1]([C:4]1[CH:37]=[CH:36][C:7]([C:8]([NH:10][C:11](=[O:35])[NH:12][C:13]2[CH:27]=[CH:26][C:16]([O:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:15]([O:28][CH2:29][O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:14]=2)=[O:9])=[CH:6][CH:5]=1)(=[NH:48])[NH2:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 23370000HCID 23370000, compound

Product 1

HCID 131719652HCID 131719652, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Example 1, t-butyl 4-[3-(4-thiocarbamoylbenzoyl)ureido]-2-(t-butoxymethoxy)phenoxyacetate (2.4 g) was reacted with iodomethane (9 ml) and acetone (130 ml) and the resultant product was treated with ammonium acetate (5 g), methanol (150 ml) and dichloromethane (150 ml) at ambient temperature. This yielded a crude solid, which was triturated with methanol, collected, washed with ether, methanol and water, and dried under high vacuum to give the title compound (1.3 g) as an off-white solid: NMR Spectrum (DMSO-d6) 1.44 (9H, s), 1.45 (9H, s), 1.77 (3H, s), 4.62 (2H, s), 4.67 (2H, s), 6.90 (1H, d), 7.09 (1H, dd), 7.29 (1H, d), 7.91 (2H, d), 8.12 (2H, d), 10.75 (1H, br s); Mass Spectrum m/Z 543 (M+H)+ ; Elemental Analysis: calculated for C27H34N4O8. 1.0 CH3CO2H. 1.25 H2O: C, 55.7%; H, 6.5%; N, 9.0%; found: C, 55.6%; H, 6.1%; N, 8.9%.

Workup

  1. customThis yielded a crude solid, which
  2. customwas triturated with methanol
  3. customcollected
  4. washwashed with ether, methanol and water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-51b57ee6a18147b48e112348a46e140d
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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