Ethanol → HCID 86746041, compound

HRID 846311Notes

Reaction equation

HRID 846311 reaction equation
[N:1]#[N:2].[C:3]([C@@H:5]([NH:14][C@H:15]([C:27]([OH:29])=O)[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)#[N:4].S(=O)(=O)(O)O.[CH2:35]([OH:37])[CH3:36].[OH-:38].[Na+].[OH2:40]>>[N:1]#[N:2].[C:3]([C@@H:5]([NH:14][C@H:15]([C:27]([N:4]1[CH2:3][CH2:5][CH2:6][C@H:36]1[C:35]([OH:40])=[O:37])=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:26])[C:22]([F:23])([F:24])[F:25])[CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:38])[NH2:4]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 86746040HCID 86746040, compound

Product 1

HCID 86746041HCID 86746041, compound

Conditions

Temperature
0 °C

Procedure

To one gram of N2 -(1(S)-cyano-3-phenylpropyl)-N6 -trifluoroacetyl-L-lysine were added 35 ml of 25 N sulfuric acid and 5 ml of ethanol at 0° C. followed by stirring for 10 hours at 0° C. and after adding thereto 100 ml of water while cooling it well, the pH thereof was adjusted to about 4.5 with 6N sodium hydroxide. The reaction product formed was washed with 100 ml of ether, extracted thrice each with 100 ml of methylene chloride, the extract was dried by anhydrous sodium sulfate, and then the solvent was distilled off to provide 720 ml of N2 -(1(S)-carbamyl-3-phenylpropyl)-N6 -trifluoroacetyl-L-lysyl-L-proline.

Workup

  1. additionafter adding
  2. customThe reaction product formed
  3. washwas washed with 100 ml of ether
  4. extractionextracted thrice each with 100 ml of methylene chloride
  5. dry with materialthe extract was dried by anhydrous sodium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-58ef805655eb48a2abb5bf5826086134
Source dataset
uspto-grants-1992_08
Patent number
US05136044

Reaction notes

Loading…