Dichloromethane → 4-Benzyloxybenzamide

HRID 2287986Notes

Reaction equation

HRID 2287986 reaction equation
FC(F)(F)C(O)=O.ClCCl.[CH2:11]([O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([N:30](CC)CC)C>>[CH2:11]([O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH2:30])=[O:24])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 37664104-Benzyloxybenzoylchloride

Product 1

HCID 27264314-Benzyloxybenzamide

Procedure

A solution of 3R-carboxylate-6-nitro-2H-3,4-dihydro-[2-1b]imidazopyran (Example 21, 1 eq.), triethylamine (1 eq.), diphenylphosphoryl azide (1 eq.) in toluene is heated at 80° C. for 4 h, cooled and t-butanol is added. The reaction is warmed to 70° C. for an additional 1 h. Workup in the standard fashion gives the Boc amine. Deprotection of the Boc group (trifluoroacetic acid:dichloromethane, 1:1) and addition of 4-benzyloxybenzoyl chloride and triethylamine gives the 4-benzyloxybenzamide of 3R-amino-6-nitro-2H-3,4-dihydro-[2-1b]imidazopyran.

Sources & evidence

ORD record
ord-9a395a53875342bea4d103d19cd2f2e7
Source dataset
uspto-grants-2000_07
Patent number
US06087358

Reaction notes

Loading…