Hydroxyamine hydrochloride → 2-Amino-4-(methylsulfanyl)butanimidic acid

HRID 890932Notes

Reaction equation

HRID 890932 reaction equation
C(S(N[C@@H](C([NH:19][C@H:20]([C:25]([NH:27]CC1C=CC(C#N)=CC=1)=[O:26])[CH2:21][CH2:22][S:23][CH3:24])=O)[C@@H](CC)C)(=O)=O)C1C=CC=CC=1.Cl.ON>C(O)C.N1C=CC=CC=1>[NH2:19][C@H:20]([C:25]([NH2:27])=[O:26])[CH2:21][CH2:22][S:23][CH3:24]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 69623752HCID 69623752, compound

Product 1

HCID 1464802-Amino-4-(methylsulfanyl)butanimidic acidYield 1.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

N-(Benzylsulfonyl)-D-isoleucyl-N1-(4-cyanobenzyl)-L-methioninamide (100 mg, 0.19 mmol) was dissolved in ethanol (6 ml) and pyridine (0.6 ml), to which hydroxyamine hydrochloride (120 mg) was then added and stirred for 16 hours. After the solvent was distilled off under reduced pressure, the residue was dissolved in ethanol, filtered and then purified by preparative HPLC to give N-(benzylsulfonyl)-D-isoleucyl-N1-[4-(E)-amino(hydroxyimino)methyl]benzyl]-L-methioninamide (1.6 mg, 0.00003 mmol; yield 1.5%).

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in ethanol
  3. filtrationfiltered
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-cdf9f1b1bfa748359e56fcd9f14cc359
Source dataset
uspto-grants-2006_02
Patent number
US07001887B2

Reaction notes

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