Triethylamine → HCID 15600358, compound

HRID 355324Notes

Reaction equation

HRID 355324 reaction equation
[NH:1]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:2][C:3]([NH:5][C@H:6]([C:8]([OH:10])=O)[CH3:7])=[O:4].[NH2:21][C@H:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25].Cl.C(N(CC)CC)C.C(OP(C#N)(=O)OCC)C>ClCCl>[NH:1]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:2][C:3]([NH:5][C@H:6]([C:8]([NH:21][C@H:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:10])[CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 2723695Leucine methyl ester hydrochlorideHCID 6994034Z-Gly-ala-OH

Product 1

HCID 15600358HCID 15600358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Z-Gly-Ala-OH (3) (20.0 g, 0.071M) and Leu-OMe.HCl (12.9 g, 0.071M) in 250 ml dichloromethane was added 21.9 ml (0.157M) triethylamine (TEA) dropwise over a period of 10 min. This addition was followed by the addition of 11.9 ml (0.078M) of diethylcyanophosphonate (DECP). The mixture was stirred overnight and the solvent removed. The residue was dissolved in ethyl acetate and washed with 1N HCl, saturated NaHCO3, and brine. The solution was dried with MgSO4, filtered and the solvent removed. Recovered 29.0 g of product that is homogeneous by TLC. 13C NMR (CDCl3) 15.93, 18.60, 21.77, 22.69, 24.72, 40.80, 44.20, 48.70, 50.87, 52.13, 65.28, 66.84, 127.92, 128.00, 128.41, 136.36, 156.76, 169.31, 172.58, 173.24.

Workup

  1. additionThis addition
  2. customthe solvent removed
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1N HCl, saturated NaHCO3, and brine
  5. dry with materialThe solution was dried with MgSO4
  6. filtrationfiltered
  7. customthe solvent removed
  8. customRecovered 29.0 g of product that

Sources & evidence

ORD record
ord-cf13b89adee3488398b3a025b9f3157c
Source dataset
uspto-grants-1998_11
Patent number
US05830840

Reaction notes

Loading…