Hydrochloric Acid → HCID 178448347, compound

HRID 1395814Notes

Reaction equation

HRID 1395814 reaction equation
C[O:2][C:3](=[O:47])[C@H:4]([CH2:39][C:40]1[CH:45]=[CH:44][C:43]([OH:46])=[CH:42][CH:41]=1)[NH:5][C:6](=[O:38])[C@H:7]([CH:35]([CH3:37])[CH3:36])[NH:8][C:9](=[O:34])[C@H:10]([CH2:27][CH2:28][CH2:29][NH:30][C:31](=[NH:33])[NH2:32])[N:11]([C:15](=[O:26])[CH2:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH3:18])[N+:12]([O-:14])=[O:13].[OH-].[Li+].Cl>CO>[C:22]([O:21][C:19]([N:17]([CH2:16][C:15]([N:11]([N+:12]([O-:14])=[O:13])[C@H:10]([C:9]([NH:8][C@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:47])=[O:2])[CH2:39][C:40]1[CH:41]=[CH:42][C:43]([OH:46])=[CH:44][CH:45]=1)=[O:38])[CH:35]([CH3:36])[CH3:37])=[O:34])[CH2:27][CH2:28][CH2:29][NH:30][C:31](=[NH:32])[NH2:33])=[O:26])[CH3:18])=[O:20])([CH3:24])([CH3:25])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178501375HCID 178501375, compound

Product 1

HCID 178448347HCID 178448347, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10.0 g of t-butoxycarbonylsarcosylnitroarginylvalyltyrosine methyl ester is dissolved in 30 ml of methanol. To this solution is added 60 ml of 1 N lithium hydroxide. The reaction mixture is stirred for three hours, then neutralized with 1 N hydrochloric acid to pH 7. The solvent is removed by vacuum and the residue is dissolved in N,N-dimethylformamide. The solution is filtered and the solvent removed by vacuum. The residue is dissolved in methanol/2-propanol. The alcohol solution is added to 1 liter of cold rapidly stirring ethyl ether. The white precipitate is filtered and dried in vacuo to afford t-butoxycarbonylsarcosylnitroarginylvalyltyrosine.

Workup

  1. customThe solvent is removed by vacuum
  2. dissolutionthe residue is dissolved in N,N-dimethylformamide
  3. filtrationThe solution is filtered
  4. customthe solvent removed by vacuum
  5. dissolutionThe residue is dissolved in methanol/2-propanol
  6. additionThe alcohol solution is added to 1 liter of cold rapidly stirring ethyl ether
  7. filtrationThe white precipitate is filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-a6240c34dd0949ffb19903d27ea79d7f
Source dataset
uspto-grants-1980_05
Patent number
US04204991

Reaction notes

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