Diethyl cyanophosphonate → HCID 86590717, compound

HRID 1860044Notes

Reaction equation

HRID 1860044 reaction equation
C(O[C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:29][C:30]2[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=2)[C:20]([O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[O:21])=[CH:14][CH:13]=1)=[O:7])(C)(C)C.[N:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[C:45]1[CH:53]=[CH:52][C:48](C(O)=O)=[CH:47][CH:46]=1.C(P(=O)(OCC)OCC)#N>C(N(CC)CC)C>[CH:36]([C:33]1[CH:32]=[CH:31][C:30]([O:29][C@@H:19]([CH2:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[C:48]3[CH:47]=[CH:46][C:45]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][N:39]=4)=[CH:53][CH:52]=3)=[CH:13][CH:14]=2)[C:20]([O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[O:21])=[CH:35][CH:34]=1)([CH3:37])[CH3:38]

Participants

5

Reactant 3

HCID 76257Diethyl cyanophosphonateHCID 8216924-(2-Pyridyl)Benzoic AcidHCID 86758864HCID 86758864, compound

Product 1

HCID 86590717HCID 86590717, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a similar manner to that described in Example 73, a reaction was carried out using 2-trimethylsilylethyl (S)-3-[4-(2-t-butoxycarbonylaminoethoxy)phenyl]-2-(4-isopropylphenoxy)propionate (0.95 g), 4-pyridine-2-ylbenzoic acid (382 mg), diethyl cyanophosphonate (0.29 ml) and triethylamine (0.53 ml) and the reaction mixture was treated to afford the title compound (0.62 g) as a colorless oil.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-f868c275b7ad43c18b499c3151304737
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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