Hydrochloric Acid → HCID 178455969, compound

HRID 1395817Notes

Reaction equation

HRID 1395817 reaction equation
C[O:2][C:3](=[O:27])[C@H:4]([CH2:21][C:22]1[N:26]=[CH:25][NH:24][CH:23]=1)[NH:5][C:6](=[O:20])[C@H:7]([C@H:16]([CH2:18][CH3:19])[CH3:17])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[OH-].[Li+].[ClH:30]>CO>[ClH:30].[C:12]([O:11][C:9]([NH:8][C@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:27])=[O:2])[CH2:21][C:22]1[N:26]=[CH:25][NH:24][CH:23]=1)=[O:20])[C@H:16]([CH2:18][CH3:19])[CH3:17])=[O:10])([CH3:14])([CH3:15])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178455968HCID 178455968, compound

Product 1

HCID 178455969HCID 178455969, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

29.4 g of t-butoxycarbonylisoleucylhistidine methyl ester is dissolved in 150 ml of methanol. To this solution is added 308 ml of 1 N lithium hydroxide. The reaction mixture is stirred for three hours, then neutralized with 1 N hydrochloride acid to pH 3. 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 2 liters of cold rapidly stirring ethyl ether. The white precipitate is filtered and dried in vacuo to afford t-butoxycarbonylisoleucylhistidine hydrochloride.

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 2 liters of cold rapidly stirring ethyl ether
  7. filtrationThe white precipitate is filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-e9333d58926b46e7819169fd760a8527
Source dataset
uspto-grants-1980_05
Patent number
US04204991

Reaction notes

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