Hydrochloric Acid → HCID 10405908, compound

HRID 1609011Notes

Reaction equation

HRID 1609011 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([C:8]([NH:10][CH2:11][C:12]([C:14]2[CH:25]=[CH:24][C:17]([O:18][CH2:19][C:20]([O:22]C)=[O:21])=[CH:16][CH:15]=2)=[O:13])=[O:9])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].C(=O)([O-])[O-].[K+].[K+].C(O)C.Cl>O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH2:11][C:12]([C:14]2[CH:25]=[CH:24][C:17]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:16][CH:15]=2)=[O:13])=[O:9])=[CH:26][CH:27]=1)(=[NH:2])[NH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 11430Potassium CarbonateHCID 10361733HCID 10361733, compound

Product 1

HCID 10405908HCID 10405908, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 80 mg of methyl p-(p-amidinobenzamidoacetyl)phenoxyacetate (Example 25), 40 mg of potassium carbonate, 10 ml of ethanol and 4 ml of water was stirred at room temperature under argon for 4 hours. 10 ml of water were then added to the mixture, which was neutralized to pH 6 with 1 N HCl. It was concentrated to 10 ml in vacuo and left to stand in a refrigerator overnight. The precipitate which had separated out was filtered off with suction and dried over KOH in vacuo at 50° C. 52 mg of amorphous p-(p-amidinobenzamidoacetyl)phenoxyacetic acid were obtained, IR bands (KBr) at 3354, 3286, 3042, 1647, 1598, 1542, 1485, 1422, 1360, 1232, 1177, 994 and 710 cm1.

Workup

  1. concentrationIt was concentrated to 10 ml in vacuo
  2. waitleft
  3. customto stand in a refrigerator overnight
  4. customThe precipitate which had separated out
  5. filtrationwas filtered off with suction
  6. dry with materialdried over KOH in vacuo at 50° C

Sources & evidence

ORD record
ord-1d2b621fefa94a2f975ebcbe9eff3197
Source dataset
uspto-grants-1995_03
Patent number
US05399585

Reaction notes

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