Acetic Acid → Diphenyl 1-(n-benzyloxycarbonylamino)-2-(4-cyanophenyl)ethanephosphonate

HRID 2293056

反応式

HRID 2293056 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]=O)=[CH:5][CH:4]=1)#[N:2].[C:12](=[O:22])([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH2:13].[C:23]1([O:29][P:30]([O:38]C2C=CC=CC=2)[O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:15]([O:14][C:12]([NH:13][CH:10]([P:30]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:38])[O:29][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 7540Triphenyl phosphite2 回HCID 12136Benzyl carbamateHCID 125916704-(2-Oxoethyl)benzonitrile2 回

生成物 1

HCID 21849067Diphenyl 1-(n-benzyloxycarbonylamino)-2-(4-cyanophenyl)ethanephosphonate収率 25%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

This compound was synthesized from crude 4-cyanophenylacetaldehyde, benzyl carbamate, and triphenylphosphite using a modification of the previously described amidoalkylation procedure.9Benzyl carbamate (6.1 g, 40 mmole) and 4-cyanophenylacetaldehyde (4.7 g, 32 mmole) were dissolved in 50 mL toluene and refluxed for 1 h. The toluene was evaporated, glacial acetic acid (10 mL) and triphenyl phosphite (8.5 mL, 32 mmole) were added to the residue, and the mixture was heated at 80 ° C. for 2 h. The volatile materials were removed by evaporation in vacuo and the resulting oil was dissolved in 50 mL methanol. The solution was refrigerated overnight and the white precipitate was filtered, dried, and recrystallized from 50 mL hot methanol. The undissolved product was discarded, and the filtrate was cooled down to give white crystals, yield 25-35%; mp 136°-137° C.; 1H NMR (DMSO) δ8.20 (d, 1H), 7.75 (d, 2H), 7.54 (d, 2H), 7.35 (m, 5H), 7.3-7.1 (m, 10H), 4.95 (q, 2H), 4.60 (m, 1H), 3.4-3.0 (m, 2H); MS (FAB+) m/e 513 (m+1). Anal. (C29H25N2O5P) C, H, N.

後処理

  1. temperaturerefluxed for 1 h
  2. customThe toluene was evaporated
  3. customThe volatile materials were removed by evaporation in vacuo
  4. dissolutionthe resulting oil was dissolved in 50 mL methanol
  5. filtrationthe white precipitate was filtered
  6. customdried
  7. customrecrystallized from 50 mL hot methanol
  8. temperaturethe filtrate was cooled down
  9. customto give white crystals, yield 25-35%

出典と根拠

ORDレコード
ord-cdfba0fe76ff42b2841c7c94b2747647
出典データセット
uspto-grants-1997_11
特許番号
US05686419

関連ノート

読み込み中…