Triethylamine → HCID 18461302, compound

HRID 2303803Notes

Reaction equation

HRID 2303803 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2(C3C=CC(O)=CC=3)[CH:14]=[CH:13][CH:12]=[CH:11][CH2:10]2)=[CH:4][C:3]=1[N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].[O:31]=[C:32]1[NH:36][C:35](=[O:37])[CH:34]([CH2:38][C:39]2[CH:49]=[CH:48][C:42]([O:43][CH2:44][C:45]([OH:47])=O)=[CH:41][CH:40]=2)[S:33]1.C(N([CH2:55][CH3:56])CC)C>O1CCCC1>[O:31]=[C:32]1[NH:36][C:35](=[O:37])[CH:34]([CH2:38][C:39]2[CH:40]=[CH:41][C:42]([O:43][CH2:44][C:45]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([O:8][C:9]4[CH:14]=[CH:13][C:12]([C:56]5[CH:55]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=5)=[CH:11][CH:10]=4)=[CH:4][C:3]=3[N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:47])=[CH:48][CH:49]=2)[S:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 113234852-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acidHCID 18461450HCID 18461450, compound

Product 1

HCID 18461302HCID 18461302, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of t-butyl N-[2-amino-5-(4′-hydroxybiphenyl-1-yloxy)phenyl]-N-methylcarbamate (0.61 g), 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (0.51 g), diethyl cyanophsphonate (0.29 g), triethylamine (0.18 g) and anhydrous tetrahydrofuran (10 ml) was stirred at ambient temperature for 2 days. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was dried over anhydrous sodium sulfate. The ethyl acetate was distilled off under reduced pressure and the residue was purified by chromatography on a silica gel column using n-hexane/ethyl acetate=1/1 as the eluant to give the desired product.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  4. distillationThe ethyl acetate was distilled off under reduced pressure
  5. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-1e9fd8a4195144bb8dcb192bfd2ccaf6
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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