Water → Ethyl 4-(4-methoxy-4-oxobutyl)-8-{[4-(4-phenylbutoxy)benzyl]amino}-3,4-dihydro-2h-1,4-benzoxazine-2-carboxylate

HRID 1882192Notes

Reaction equation

HRID 1882192 reaction equation
[NH2:1][C:2]1[C:11]2[O:10][CH:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8][N:7]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:24]1([CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:35]2[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[CH3:23][O:22][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][N:7]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([NH:1][CH2:39][C:38]3[CH:41]=[CH:42][C:35]([O:34][CH2:33][CH2:32][CH2:31][CH2:30][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:36][CH:37]=3)[C:11]=2[O:10][CH:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 158710154-(4-Phenylbutoxy)benzaldehydeHCID 23124760Ethyl 8-amino-4-(4-methoxy-4-oxobutyl)-3,4-dihydro-2h-1,4-benzoxazine-2-carboxylate

Product 1

HCID 23124624Ethyl 4-(4-methoxy-4-oxobutyl)-8-{[4-(4-phenylbutoxy)benzyl]amino}-3,4-dihydro-2h-1,4-benzoxazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Ethyl 8-amino-4-(4-methoxy-4-oxobutyl)-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate (80 mg; prepared by subjecting the compound prepared in Example 3 to the same procedure as described in Example 29) and 4-(4-phenylbutoxy)benzaldehyde (60 mg) were dissolved in 1,2-dichloroethane (4 mL), and to this solution was added sodium triacetoxyborohydride (96 mg) with ice cooling, and the mixture was stirred for 2 hours at room temperature. To the reaction mixture was added water and the resulting mixture was extracted with ethyl acetate. The extract was washed sequentially with a saturated aqueous solution of sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=8:2) to give the title compound (121 mg) having the following physical data.

Workup

  1. customprepared
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed sequentially with a saturated aqueous solution of sodium bicarbonate and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-64448df3b90b41dd85a1080fb9dc5305
Source dataset
uspto-grants-2012_11
Patent number
US08318952B2

Reaction notes

Loading…