Diethyl cyanophosphonate → HCID 88118032, compound

HRID 413779Notes

Reaction equation

HRID 413779 reaction equation
[C:1]([O:5][C:6](=[O:18])[N:7]([C:9]1[CH:14]=[C:13]([S:15][CH3:16])[CH:12]=[CH:11][C:10]=1[NH2:17])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[O:19]=[C:20]1[NH:24][C:23](=[O:25])[CH:22]([CH2:26][C:27]2[CH:37]=[CH:36][C:30]([O:31][CH2:32][C:33](O)=[O:34])=[CH:29][CH:28]=2)[S:21]1.C(P(=O)(OCC)OCC)#N>C(N(CC)CC)C.O1CCCC1>[C:1]([O:5][C:6](=[O:18])[N:7]([C:9]1[CH:14]=[C:13]([S:15][CH3:16])[CH:12]=[CH:11][C:10]=1[NH:17][C:33](=[O:34])[CH2:32][O:31][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][CH:22]2[S:21][C:20](=[O:19])[NH:24][C:23]2=[O:25])=[CH:37][CH:36]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 76257Diethyl cyanophosphonate2×HCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acid2×HCID 12069416HCID 12069416, compound

Product 1

HCID 88118032HCID 88118032, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Procedure

To a mixture of N-(2-amino-5-methylthiophenyl)-N-methylcarbamic acid t-butyl ester (2.0 g) (obtained in Reference Example 4), 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (2.31 g) (obtained in Reference Example 6), triethylamine (1.14 ml) and anhydrous tetrahydrofuran (40 ml) was added diethyl cyanophosphonate (1.34 g) and the resulting mixture was stirred at room temperature for 4 hours and allowed to stand overnight. To the reaction mixture were further added 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (0.84 g), triethylamine (0.3 g) and diethyl cyanophosphate (0.49 g) and the resulting solution was stirred at room temperature for 1.5 hours. At the end of this time the reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The resulting residue was chromatographed on a silica gel column using n-hexane/ethyl acetate (2/1) as the eluant to give the desired product (3.54 g).

Workup

  1. waitto stand overnight
  2. stirringthe resulting solution was stirred at room temperature for 1.5 hours
  3. concentrationAt the end of this time the reaction mixture was concentrated
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customThe resulting residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-a27ec639854d49f7bf7dd32cd5640db5
Source dataset
uspto-grants-2003_05
Patent number
US06569877B2

Reaction notes

Loading…