Triethylamine → HCID 86585959, compound

HRID 413777Notes

Reaction equation

HRID 413777 reaction equation
[C:1]([O:5][C:6](=[O:17])[N:7]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH2:16])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[O:18]=[C:19]1[NH:23][C:22](=[O:24])[CH:21]([CH2:25][C:26]2[CH:36]=[CH:35][C:29]([O:30][CH2:31][C:32](O)=[O:33])=[CH:28][CH:27]=2)[S:20]1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>O1CCCC1>[C:1]([O:5][C:6](=[O:17])[N:7]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH:16][C:32](=[O:33])[CH2:31][O:30][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][CH:21]2[S:20][C:19](=[O:18])[NH:23][C:22]2=[O:24])=[CH:36][CH:35]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acidHCID 12069414HCID 12069414, compound

Product 1

HCID 86585959HCID 86585959, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-(2-amino-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (2.50 g) (obtained in Reference Example 2), 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (3.01 g) (obtained in Reference Example 6), triethylamine (1.49 ml) and anhydrous tetrahydrofuran (50 ml) was added diethyl cyanophosphonate (1.75 g) and the resulting mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated and the residue 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 (3.26 g). Rf=0.41 (thin-layer chromatography on a silica gel plate using n-hexane/ethyl acetate (2/3) as the eluant).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe resulting residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-5636505589704a6d93edf12a700cce96
Source dataset
uspto-grants-2003_05
Patent number
US06569877B2

Reaction notes

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