Methyl acetoacetate → HCID 57722730、化合物

HRID 1986893ノート

反応式

HRID 1986893 の反応式
[H-].[Na+].[C:3]([O:9][CH3:10])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].[CH2:11]([O:13][C:14]1[O:15][C:16](=[O:28])[C:17]2[CH:27]=[C:26]3[C:21]([CH2:22][CH2:23][CH2:24][CH2:25]3)=[CH:20][C:18]=2[N:19]=1)[CH3:12]>C1C=CC=CC=1>[C:5](/[C:4](=[C:16](\[C:17]1[C:18]([NH:19][C:14]([O:13][CH2:11][CH3:12])=[O:15])=[CH:20][C:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=2[CH:27]=1)/[OH:28])/[C:3]([O:9][CH3:10])=[O:8])(=[O:6])[CH3:7]

参加物

5

反応物 3

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 57722727HCID 57722727、化合物

生成物 1

HCID 57722730HCID 57722730、化合物

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
23 °C

実験手順

To a dispersion of sodium hydride (95%) (0.80 g, 33 mmol, 2.1 equiv) in anhydrous benzene (100 mL) under nitrogen was added dropwise methyl acetoacetate (5.0 mL, 5.4 g, 46 mmol, 2.9 equiv) and the resulting mixture was stirred at 23° C. for 1 h. 2-ethoxy-6,7,8,9-tetrahydro-4H-naphtho[2,3-d][1,3]oxazin-4-one (1-3) (3.8 g, 16 mmol, 1 equiv) was added and the reaction mixture was stirred for 20 h. The excess sodium hydride was quenched with water and the organic layer was separated, extracted three times with water and the combined aqueous layers were made acidic with concentrated hydrochloric acid solution. The resulting precipitate was filtered and dried to yield methyl (2Z)-2-acetyl-3-{3-[(ethoxycarbonyl)amino]-5,6,7,8-tetrahydronaphthalen-2-yl}-3-hydroxyprop-2-enoate (1-4) as a yellow oil. LRMS m/z (M+H) 362.5 found, 362.2 required.

後処理

  1. stirringthe reaction mixture was stirred for 20 h
  2. customThe excess sodium hydride was quenched with water
  3. customthe organic layer was separated
  4. extractionextracted three times with water
  5. filtrationThe resulting precipitate was filtered
  6. customdried

出典と根拠

ORDレコード
ord-a1c259983e194b89af95847ef13b126d
出典データセット
uspto-grants-2009_06
特許番号
US07550477B2

反応ノート

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