HCID 18536546, compound → HCID 69696270, compound

HRID 412613Notes

Reaction equation

HRID 412613 reaction equation
C([O:5][C:6](=[O:42])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[NH:17][C:18](=[O:41])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]2)=[CH:23][CH:22]=1)(C)(C)C>C(O)(=O)C>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([NH:8][CH2:7][C:6]([OH:42])=[O:5])=[C:10]([NH:17][C:18](=[O:41])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:23][CH:22]=2)[CH:11]=1)#[N:16]

Participants

3

Reactant 1

HCID 18536546HCID 18536546, compound

Product 1

HCID 69696270HCID 69696270, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-[4-cyano-2-[4-(1-tert-butoxycarbonylpiperidin-4-yloxy)phenoxyacetamido]phenyl]glycine tert-butyl ester (16.91 g) in acetic acid (500 ml) was stirred at 75° C. for 12 hours. The solvent was evaporated and to the obtained residue was added trifluoroacetic acid (100 ml), and the mixture was stirred at room temperature for 30 min. After completion of the reaction, the solvent was evaporated. To the obtained residue was added ice and then aqueous sodium hydroxide solution and the resultant solid was collected by filtration and washed successively with water and ethyl acetate to give N-[4-cyano-2-[4-(piperidin-4-yloxy)phenoxyacetamido]phenyl]glycine (8.642 g). In the same manner as in Example 1, Step 1, the title compound (9.506 g) was obtained from this compound, di-tert-butyl dicarbonate (6.96 g) and 1N aqueous sodium hydroxide solution (23.4 ml).

Workup

  1. customThe solvent was evaporated and to the obtained residue
  2. additionwas added trifluoroacetic acid (100 ml)
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated
  5. additionTo the obtained residue was added ice
  6. filtrationaqueous sodium hydroxide solution and the resultant solid was collected by filtration
  7. washwashed successively with water and ethyl acetate

Sources & evidence

ORD record
ord-19e625daefdf475289d5cb597994734b
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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