Potassium Hydroxide → 2-(3-tert-Butoxycarbonylaminopropoxy)-4-(morpholin-4-yl)benzoic Acid

HRID 644249ノート

反応式

HRID 644249 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:20]=[CH:19][C:14]=1[C:15]([O:17]C)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[C:21]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[CH:20]=[CH:19][C:14]=1[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 57602457Methyl 2-(3-tert-butoxycarbonylaminopropoxy)-4-(morpholin-4-yl)benzoate

生成物 1

HCID 576025002-(3-tert-Butoxycarbonylaminopropoxy)-4-(morpholin-4-yl)benzoic Acid収率 99.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

The methyl 2-[3-(tert-butoxycarbonylamino)propoxy]-4-(morpholin-4-yl)benzoate (2.34 g, 5.93 mmol) was diluted with ethanol (60 mL) and water (60 mL). Potassium hydroxide pellets (1.64 g, 29.2 mmol) were added and the resulting mixture was heated to 70° C. After 2 hours, the reaction was concentrated in vacuo. The residue was diluted with methylene chloride (200 mL) and extracted with saturated aqueous citric acid (2×50 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated to give the desired product (2.24 g, 5.90 mmol, 99%). 1NMR (300 MHz, DMSO-d6): δ 7.59 (d, J=8.7 Hz, 1H); 6.85 (m, 1H); 6.49 (m, 2H); 4.00 (t, J=5.9 Hz, 2H); 3.68 (m, 4H); 3.21 (m, 4H); 3.07 (m, 2H); 1.79 (t, J=6.2 Hz, 2H); 1.33 (s, 9H). IS-MS m/e: 381.4 (m+1).

後処理

  1. additionwere added
  2. concentrationthe reaction was concentrated in vacuo
  3. additionThe residue was diluted with methylene chloride (200 mL)
  4. extractionextracted with saturated aqueous citric acid (2×50 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-d10a851e10c44d28b52f1eda9fbed568
出典データセット
uspto-grants-2010_04
特許番号
US07700628B2

反応ノート

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