Potassium Carbonate → HCID 59751112、化合物

HRID 749000

反応式

HRID 749000 の反応式
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1.[C:16]([O:20][C:21]([NH:23][CH:24]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[C:25]([OH:27])=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C.O>[C:16]([O:20][C:21]([NH:23][CH:24]([C:28]1[CH:33]=[CH:32][C:31]([O:34][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)=[CH:30][CH:29]=1)[C:25]([OH:27])=[O:26])=[O:22])([CH3:19])([CH3:17])[CH3:18]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 4189925N-Boc-4-Hydroxyphenyl-DL-glycine

生成物 1

HCID 59751112HCID 59751112、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

Potassium carbonate (23.11 g, 140 mmol) and 4-fluorobenzaldehyde (25.0 mL, 233 mmol) were added to a solution of tert-butoxycarbonylamino-(4-hydroxy-phenyl)-acetic acid (12.5 g, 46.7 mmol) in anhydrous DMF (40 mL). The resulting suspension was refluxed at 75±5° C. under an atmosphere of argon. After 72 hr, the reaction mixture was cooled to room temperature, diluted with water (200 mL) and extracted with EtOAc (2×150 mL). The aqueous layer was collected, acidified with 5.0 M HCl to pH ˜2.0 and extracted with EtOAc (3×150 mL). The resulting EtOAc layer was extracted with water (2×300 mL) and brine (1×300 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to yield the desired aldehyde 29 as a low melting solid (12.0 g, 69%). 1H NMR (400 MHz, DMSO-d6): 12.9 (br, 1H), 9.93 (s, 1H), 7.93 (d, J=8.8 Hz, 2H), 7.65 (d, J=8.8 Hz, 1H), 7.49 (d, J=8.8 Hz, 2H), 7.13 (overlapped d, J=8.8 Hz, 2H), 7.13 (overlapped d, J=8.8 Hz, 2H), 5.16 (d, J=8.0 Hz, 1H), 1.40 (s, 9H).

後処理

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (2×150 mL)
  3. customThe aqueous layer was collected
  4. extractionextracted with EtOAc (3×150 mL)
  5. extractionThe resulting EtOAc layer was extracted with water (2×300 mL) and brine (1×300 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-cc57aa505e8d4e4b98c6daa977ac0fd5
出典データセット
uspto-grants-2008_07
特許番号
US07399786B2

関連ノート

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