Hydrochloric Acid → HCID 178512948, compound

HRID 543152Notes

Reaction equation

HRID 543152 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([C:21]([OH:23])=[O:22])[CH2:9][C:10]([C@@H:12]([NH2:20])[CH2:13][CH2:14][CH2:15][N:16]=[C:17]([NH2:19])[NH2:18])=[O:11])=[CH:3][CH:2]=1.Cl.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>O.C(OCC)C>[C:25]([NH:20][CH:12]([CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH2:19])=[NH:18])[C:10](=[O:11])[CH2:9][CH:8]([CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[C:21]([OH:23])=[O:22])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 5487157Benzenepropanoic acid, alpha-[3-amino-6-[(aminoiminomethyl)amino]-2-oxohexyl]-, monohydrochloride, [S-(R*,S*)]-

Product 1

HCID 178512948HCID 178512948, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Arphamenine A hydrochloride (200 mg) was dissolved in 1 ml of water, and to the resulting solution were added 98 μl of benzoyl chloride and 119 mg of sodium carbonate, each in 1/5 portions at 30 minutes-interval and totally five times, under ice-cooling and stirring. After the reaction was completed, the reaction mixture was adjusted to pH 7.0 with 1N HCl, followed by addition of ethyl ether thereto. The precipitate as formed was washed with water and dried to give 225 mg of the titled compound as a colorless powder. This product gave a value of m/z 425 (MH+) in mass spectrometry.

Workup

  1. temperatureunder ice-cooling
  2. customThe precipitate as formed
  3. washwas washed with water
  4. customdried

Sources & evidence

ORD record
ord-1de2ed6c43b447058a752a0439e65381
Source dataset
uspto-grants-1987_04
Patent number
US04661495

Reaction notes

Loading…