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

HRID 1882192ノート

反応式

HRID 1882192 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-64448df3b90b41dd85a1080fb9dc5305
出典データセット
uspto-grants-2012_11
特許番号
US08318952B2

反応ノート

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