Triethylamine → HCID 18461441, compound

HRID 2303756Notes

Reaction equation

HRID 2303756 reaction equation
C(P(=O)(OCC)OCC)#N.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[C:23]([CH3:25])[C:22]([O:26][CH2:27][O:28][CH3:29])=[C:21]([CH3:30])[C:20]=2[CH3:31])=[CH:14][C:13]=1[N:32]([CH3:40])[C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].[O:41]=[C:42]1[NH:46][C:45](=[O:47])[CH:44]([CH2:48][C:49]2[CH:59]=[CH:58][C:52]([O:53][CH2:54][C:55](O)=[O:56])=[CH:51][CH:50]=2)[S:43]1.C(N(CC)CC)C>O1CCCC1>[O:41]=[C:42]1[NH:46][C:45](=[O:47])[CH:44]([CH2:48][C:49]2[CH:50]=[CH:51][C:52]([O:53][CH2:54][C:55]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[C:23]([CH3:25])[C:22]([O:26][CH2:27][O:28][CH3:29])=[C:21]([CH3:30])[C:20]=4[CH3:31])=[CH:14][C:13]=3[N:32]([CH3:40])[C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:56])=[CH:58][CH:59]=2)[S:43]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acidHCID 18461355t-Butyl N-[2-amino-5-(4-methoxymethoxy-2,3,5-trimethylphenoxy)phenyl]N-methylcarbamate

Product 1

HCID 18461441HCID 18461441, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.34 g of diethyl cyanophosphonate were added to a mixture of 18.7 g of t-butyl N-[2-amino-5-(4-methoxymethoxy-2,3,5-trimethylphenoxy)phenyl]-N-methylcarbamate, 12.6 g of 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid, 4.55 g of triethylamine and 300 ml of anhydrous tetrahydrofuran. The resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated by evaporation. Water was then added to the concentrate. After extraction with ethyl acetate, the extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=1/1), whereby 23.1 g of the desired compound were obtained.

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation
  2. additionWater was then added to the concentrate
  3. extractionAfter extraction with ethyl acetate
  4. dry with materialthe extract was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-dcc273650ee24bdc8612371db615b373
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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