Acetone → tert-Butyl ((trans-4-(((benzyloxy)carbonyl)amino)cyclohexyl)methyl)carbamate

HRID 917514Notes

Reaction equation

HRID 917514 reaction equation
BrC[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1OC)=[O:4].N[C:14]([NH:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:19][CH2:18]1)=S.C(N(CC)C(C)C)(C)C.CC(C)=[O:43]>>[CH2:3]([O:4][C:14](=[O:43])[NH:16][CH:17]1[CH2:22][CH2:21][CH:20]([CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:19][CH2:18]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 81531DiisopropylethylamineHCID 123440Bromomethyl 2-methoxyphenyl ketoneHCID 178453644HCID 178453644, compound

Product 1

HCID 22254006tert-Butyl ((trans-4-(((benzyloxy)carbonyl)amino)cyclohexyl)methyl)carbamateYield 44%

Procedure

A mixture of 2-bromoacetylanisole (1.5 g, 6.5 mmol), trans-4-(aminocarbothioylamino)-1-(t-butoxycarbonyl-amino)methyl-cyclohexane (1.88 g, 6.5 mmol) and N,N-diisopropylethylamine (2.3 ml, 13.1 mmol) in acetone (20 ml) was heated at reflux temperature overnight. The solvent was evaporated, the residue was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography over silica gel (hexanes/ethyl acetate 5:2) to give the desired product as a light brown oil (1.2 g, 44% yield): ESMS m/e=418 (MH+): 1H NMR δ 8.08 (dd, 1H, J=1.6, 7.7 Hz), 7.24 (m, 1H), 7.18 (s, 1H), 7.01 (t, 1H, J=7.6 Hz), 6.95 (d, 1H, J=8.2 Hz), 4.96 (d, 1H, J=8.1 Hz), 4.60 (m, 1H), 3.93 (s, 3H), 3.30 (m, 1H), 3.01 (t, 2H, J=6.4 Hz), 2.25 (m, 2H), 1.84 (m, 2H), 1.47 (m, 1H), 1.45 (s, 9H), 1.30-1.03 (m, 4H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature overnight
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with saturated aqueous sodium bicarbonate solution
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash column chromatography over silica gel (hexanes/ethyl acetate 5:2)

Sources & evidence

ORD record
ord-a3ff3efbad3644b9a9d0cc570abba9de
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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