Reaction #40389

ord-b454d9d260ae437a8d51681e85463c20

Reaction equation

CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2
benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one
Cc1cc(C)cc(CC(C)(C)N)c1
2-(3,5-dimethylphenyl)-1,1-dimethylethylamine
Cl
hydrochloride
→
Cc1cc(C)cc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)c1
6-benzyloxy-8-{2-[2-(3,5-dimethylphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-4H-benzo[1,4]oxazin-3-one

Reactants

CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2
benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one
Cc1cc(C)cc(CC(C)(C)N)c1
2-(3,5-dimethylphenyl)-1,1-dimethylethylamine
Cl
hydrochloride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Prepared analogously to the method for Example 8(d) from 1.47 g (4.1 mmol) of benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 0.65 g (3.7 mmol) of 2-(3,5-dimethylphenyl)-1,1-dimethylethylamine. Yield: 1.1 g (51%, hydrochloride); melting point: 220° C.-222° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07727984B2uspto-grants-2010_06