Triethylamine → HCID 88008007, compound

HRID 2303789Notes

Reaction equation

HRID 2303789 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[N:16]([CH3:24])[C:17](=O)OC(C)(C)C.[O:25]=[C:26]1[NH:30][C:29](=[O:31])[CH:28]([CH2:32][C:33]2[CH:43]=[CH:42][C:36]([O:37][CH2:38]C(O)=O)=[CH:35][CH:34]=2)[S:27]1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>O1CCCC1>[OH:15][C:12]1[CH:11]=[CH:10][C:9]([S:8][C:5]2[CH:6]=[CH:7][C:2]3[N:1]=[C:24]([CH2:38][O:37][C:36]4[CH:35]=[CH:34][C:33]([CH2:32][CH:28]5[S:27][C:26](=[O:25])[NH:30][C:29]5=[O:31])=[CH:43][CH:42]=4)[N:16]([CH3:17])[C:3]=3[CH:4]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acidHCID 18461481HCID 18461481, compound

Product 1

HCID 88008007HCID 88008007, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to that described in Example (2-1), a reaction was carried out using t-butyl N-[2-amino-5-(4-hydroxyphenylthio)phenyl]-N-methylcarbamate (2.36 g), 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (2.87 g), diethyl cyanophosphonate (1.67 g), triethylamine (1.03 g) and anhydrous tetrahydrofuran (60 ml) and the reaction mixture was purified. Then, in a similar manner to that described in Example (2-2a) a reaction was carried out using the above product and 4N hydrogen chloride/dioxane (20 ml) and the reaction mixture was purified to give the desired compound (0.72 g).

Workup

  1. customthe reaction mixture was purified
  2. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-27cd8c7a167b4f9982606bd3f13a9f54
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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