Hydrochloric Acid → HCID 54456930, compound

HRID 344657Notes

Reaction equation

HRID 344657 reaction equation
[OH-:1].[Na+].Cl.[CH:4]1([C:10]2N=C(C3CCCCC3)N([CH:21]=2)C(N2C=CN=C2)=O)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.Cl.[CH2:29]([O:31][C:32](=[O:37])[C@H:33]([CH2:35][SH:36])[NH2:34])[CH3:30]>CO.O1CCCC1.C(OCC)C.C(N(CC)CC)C>[CH2:29]([O:31][C:32](=[O:37])[C@H:33]([CH2:35][SH:36])[NH:34][C:32](=[O:37])[CH2:33][NH:34][C:7]1[CH:6]=[C:5]2[C:4]([C:10]([CH3:21])=[CH:30][C:29](=[O:31])[O:1]2)=[CH:9][CH:8]=1)[CH3:30]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723617Ethyl cysteinate hydrochlorideHCID 131717020HCID 131717020, compound

Product 1

HCID 54456930HCID 54456930, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To 1.96 g (7.5 mmol) of the above ester in 15 ml of methanol and 15 ml of tetrahydrofuran was added B 10 ml of 1N aqueous sodium hydroxide. After 30 minutes, 4 ml of 10% aqueous hydrochloric acid was added. The organic solvents were evaporated and the resultant crystalline product was filtered and washed with cold ethanol and then ether. This material was dissolved in 20 ml of tetrahydrofuran and 4 ml of dimethylformamide. Dicyclohexylcarbonyldiimidazole (1.3 g, 2.2 eq) was added and the reaction allowed to stir for 15 minutes. Cysteine ethyl ester hydrochloride (1.6 g, 2.5 eq) and triethylamine (1.2 ml) were then added. After a further three hours, the reaction was diluted with ethyl ether containing 5% methylene chloride and washed once with 10% aqueous hydrochloric acid and twice with brine. After drying with magnesium sulfate and evaporating the solvents, the crude product was crystallized by dissolving in chloroform containing a minimal amount of ethanol and then added an excess of ether. The crystals were filtered and dried to give pure N-[[(4-methyl-coumarin-7-yl)amino]acetyl]cysteine ethyl ester.

Workup

  1. customThe organic solvents were evaporated
  2. filtrationthe resultant crystalline product was filtered
  3. washwashed with cold ethanol
  4. dissolutionThis material was dissolved in 20 ml of tetrahydrofuran
  5. waitAfter a further three hours
  6. washwashed once with 10% aqueous hydrochloric acid and twice with brine
  7. dry with materialAfter drying with magnesium sulfate
  8. customevaporating the solvents
  9. customthe crude product was crystallized
  10. dissolutionby dissolving in chloroform containing a minimal amount of ethanol
  11. additionadded an excess of ether
  12. filtrationThe crystals were filtered
  13. customdried

Sources & evidence

ORD record
ord-2491f79fa7a4438e9aef352e77785494
Source dataset
uspto-grants-1991_10
Patent number
US05053394

Reaction notes

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