Ammonia → HCID 178512860, compound

HRID 972896Notes

Reaction equation

HRID 972896 reaction equation
C([S:9][CH2:10][CH2:11][C:12]([NH:14][C@H:15]([C:23]([OH:25])=[O:24])[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[NH:22])[NH2:21])=[O:13])(=O)C1C=CC=CC=1.N>O>[SH:9][CH2:10][CH2:11][C:12]([NH:14][C@H:15]([C:23]([OH:25])=[O:24])[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[NH:21])[NH2:22])=[O:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178512859HCID 178512859, compound

Product 1

HCID 178512860HCID 178512860, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Nα-(3-benzoylthiopropanoyl)-L-arginine (1 g.) is dissolved with vigorous stirring in a mixture of water (5 ml.) and concentrated ammonia (5 ml.). After one hour, the solution is extracted with ethyl acetate and concentrated to dryness in vacuo. The residue is chromatographed on a column of DEAE Sephadex [anion exchange resin derived from dextran (Mikes, supra, page 328)] (85 ml.) with a buffer of 0.005 M ammonium bicarbonate. The fractions containing the Nα-(3-mercaptoproanoyl)-L-arginine (as indicated by positive thiol and Sakaguchi Reaction) are pooled and lyophilized to remove ammonium bicarbonate, yield 200 mg., m.p. 230° (starts decomposing at 200°).

Workup

  1. extractionthe solution is extracted with ethyl acetate
  2. concentrationconcentrated to dryness in vacuo
  3. customThe residue is chromatographed on a column of DEAE Sephadex [anion exchange resin derived from dextran (Mikes, supra, page 328)] (85 ml.) with a buffer of 0.005 M ammonium bicarbonate
  4. additionThe fractions containing the Nα-(3-mercaptoproanoyl)-L-arginine (as indicated by positive thiol and Sakaguchi Reaction)
  5. customto remove ammonium bicarbonate, yield 200 mg
  6. customm.p. 230° (starts decomposing at 200°)

Sources & evidence

ORD record
ord-40149b0c3cd447d4b39aacd03a8b3b1f
Source dataset
uspto-grants-1977_10
Patent number
US04053651

Reaction notes

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