Diethyl cyanophosphonate → HCID 86587630, compound

HRID 1358584Notes

Reaction equation

HRID 1358584 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].[C:18]([CH2:21][O:22][C:23]1[CH:36]=[CH:35][C:26]([CH2:27][CH:28]2[S:32][C:31](=[O:33])[NH:30][C:29]2=[O:34])=[CH:25][CH:24]=1)(O)=[O:19].C(P(=O)(OCC)OCC)#N>O1CCCC1>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:18]([CH2:21][O:22][C:23]2[CH:36]=[CH:35][C:26]([CH2:27][CH:28]3[S:32][C:31](=[O:33])[NH:30][C:29]3=[O:34])=[CH:25][CH:24]=2)=[O:19])=[C:3]([N:9]([CH3:17])[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:4]=1

Participants

5

Reactant 3

HCID 76257Diethyl cyanophosphonateHCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acidHCID 18184944HCID 18184944, compound

Product 1

HCID 86587630HCID 86587630, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of t-butyl N-(2-amino-5-hydroxyphenyl)-N-methylcarbamate (0.43 g), 5-(4-carboxymethoxybenzyl)thiazolidine-2,4-dione (0.51 g), diethyl cyanophosphonate (0.29 g) triethylamine (0.18 g) and tetrahydrofuran (20 ml) was stirred at room temperature for 8 hours. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using hexane: ethyl acetate=2:3 as the eluant to afford t-butyl N-{5-hydroxy-2-[4-(2,4-dioxothiazolidin-5-ylmethyl) phenoxymethylcarbonylamino]phenyl}-N-methylcarbamate (0.75 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-fef4534ca6544bedab8a792591530519
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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