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

HRID 2293056

Reaction equation

HRID 2293056 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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%

Sources & evidence

ORD record
ord-cdfba0fe76ff42b2841c7c94b2747647
Source dataset
uspto-grants-1997_11
Patent number
US05686419

Linked notes

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