tert-Butanol → Tert-butyl 3-nitrophenylcarbamate
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]=[C:11]=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:13]([OH:17])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:11](=[O:12])[NH:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([CH3:16])([CH3:15])[CH3:14]Participants
Procedure
3-Nitrophenylisocyanate was reacted with tert-butanol to form (3-nitro-phenyl)-carbamic acid tert-butyl ester. This was reacted with benzyl 2-bromoacetate, then the tert-butyloxycarbonyl group was removed and the resulting (3-nitro-phenylamino)-acetic acid benzyl ester was reduced with aluminium amalgam to afford (3-amino-phenylamino)-acetic acid benzyl ester. This was reacted with 5-(2-adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) according to the procedure of Example 20, step d. The benzyl ester was hydrogenolysed using the same procedure as in Example 1, step e to afford the title compound. 1H NMR (300 MHz, d6-DMSO/D2O) 7.02-6.86 (3H, m), 6.23 (1H, d), 3.55 (2H, s), 2.83 (2H, m), 2.61 (1H, m), 1.88-1.19 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 59.09; H, 8.60; N, 9.41%. C37H57N5O8.3.0 mols H2O requires: C, 58.95; H, 8.42; N, 9.29%.
Sources & evidence
- ORD record
- ord-60d6da342dfe4b7abb762bd0bc86e3c5
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479531B1
Reaction notes
Loading…