Acetic Acid → 5-({1-[(Carboxymethyl)imino]-1-hydroxy-3-sulfanylpropan-2-yl}imino)-5-hydroxy-N-(1-hydroxyethylidene)norvaline

HRID 1867912Notes

Reaction equation

HRID 1867912 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][C:8]([NH:10][C@H:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH2:12][SH:13])=[O:9])[C:3]([OH:5])=[O:4].[C:21](OC(=O)C)(=[O:23])[CH3:22].C(O)(=O)C.C(OCC)C>O>[C:21]([NH:1][C@@H:2]([CH2:6][CH2:7][C:8]([NH:10][C@H:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])[CH2:12][SH:13])=[O:9])[C:3]([OH:5])=[O:4])(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 7918Acetic Anhydride2×HCID 124886Glutathione

Product 1

HCID 104278825-({1-[(Carboxymethyl)imino]-1-hydroxy-3-sulfanylpropan-2-yl}imino)-5-hydroxy-N-(1-hydroxyethylidene)norvalineYield 51.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of glutathione (1 g, 3.25 mmole) in 10 ml of water was added over 1 hr to a mixture of acetic anhydride (10 ml) and acetic acid (10 ml) at room temperature. After the addition was complete, the reaction mixture was chilled on ice. Additional acetic anhydride (5 ml) was added and the reaction mix was stirred while it gradually warmed to room temperature overnight. The reaction mixture was treated with 300 ml of ethyl ether and cooled overnight to obtain crystallized product. A white solid was obtained by filtering the reaction mix, and washing with more ether. More crystallized product was generated in the filtrate. The filtration and washing were repeated a second time and the white solids were combined and air-dried (585 mg, yield 51.5%).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was chilled on ice
  3. additionthe reaction mix
  4. temperaturecooled overnight
  5. customto obtain
  6. customcrystallized product
  7. customA white solid was obtained
  8. filtrationby filtering the reaction
  9. additionmix
  10. washwashing with more ether
  11. customMore crystallized product
  12. filtrationThe filtration
  13. washwashing
  14. customair-dried (585 mg, yield 51.5%)

Sources & evidence

ORD record
ord-5fb09e9acc764c87a781c2d14a8fa214
Source dataset
uspto-grants-2009_12
Patent number
US07632928B2

Reaction notes

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