Triethylamine → HCID 18444332, compound

HRID 459743Notes

Reaction equation

HRID 459743 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:18]([O:20][P:21](C#N)(=[O:25])[O:22][CH2:23][CH3:24])[CH3:19].C(N(CC)CC)C>ClCCl.O>[CH2:18]([O:20][P:21]([O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[CH:12][CH:13]=1)([O:22][CH2:23][CH3:24])=[O:25])[CH3:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

Product 1

HCID 18444332HCID 18444332, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.2 g (5 mmol) of N-Boc tyramine, 0.9 g (5.5 mmol) of diethylcyanophosphonate and 1.4 ml (10 mmol) of triethylamine are placed in solution in 5 ml of dichloromethane at 0° C. under an argon atmosphere. The reaction mixture is stirred for 30 minutes at 0° C. followed by diluting with 25 ml of water and extracting with twice 30 ml of dichloromethane. The organic phases are combined followed by washing with 50 ml of water then 25 ml of a saturated solution of sodium chloride. The organic phase is dried over magnesium sulphate, followed by filtering and concentrating under vacuum. The expected product is obtained in the form of a clear oil with a yield of 92% (1.73 g).

Workup

  1. extractionextracting with twice 30 ml of dichloromethane
  2. washby washing with 50 ml of water
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationby filtering
  5. concentrationconcentrating under vacuum

Sources & evidence

ORD record
ord-852ddb7acf1e4d4db5a0cce92dc54e78
Source dataset
uspto-grants-2007_03
Patent number
US07196084B2

Reaction notes

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