Hydrochloric Acid → Hydrochloric Acid

HRID 1283938Notes

Reaction equation

HRID 1283938 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:22]([OH:24])=[O:23])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:4].B(F)(F)F.[CH3:29]COCC.[ClH:34]>CO.C(O)C>[ClH:34].[CH3:29][O:23][C:22](=[O:24])[C@H:6]([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[NH:5][C:3](=[O:4])[CH2:2][NH2:1].[ClH:34]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 22792280HCID 22792280, compound

Product 2

HCID 313Hydrochloric AcidHCID 131710437HCID 131710437, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Nα-Glycyl-Nε-carbobenzoxy-L-lysine (10.1 g.) prepared by the method of Rao et al. (J. Biol. Chem., 198,507 1952) was dissolved in methanol (150 ml.) and treated with boron trifluoride etherate (30 ml.) and the mixture heated at 80°C for 25 hours. The solvent was removed in vacuo and the residual oil dissolved in water (100 ml.) and extracted with ether (2 × 50 ml.) and the extracts discarded. The aqueous solution was adjusted to pH 9.0 with 4N sodium hydroxide, saturated with sodium chloride and extracted with ethyl acetate (3 × 50 ml.). The combined extracts were washed with saturated brine, dried (MgSO4) and the solvent removed in vacuo to give a residual oil which was redissolved in ethanol (10 ml.) and treated with an excess of an ethereal solution of hydrogen chloride. The solid was filtered and recrystallised from isopropanol/diisopropyl ether to give Nα-glycyl-Nε-carbobenzoxy-L-lysine methyl ester hydrochloride, needles (4.5 g.) m.p. 122°C. (Found: C, 53.0; H, 6.8; N, 10.8. C17H25N3O5. HCl requires: C, 52.6; H, 6.7; N, 10.8%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residual oil dissolved in water (100 ml.)
  3. extractionextracted with ether (2 × 50 ml.)
  4. extractionextracted with ethyl acetate (3 × 50 ml.)
  5. washThe combined extracts were washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customto give a residual oil which
  9. filtrationThe solid was filtered
  10. customrecrystallised from isopropanol/diisopropyl ether

Sources & evidence

ORD record
ord-23b18cbbc88949bbaa41c2a9b66ba1e6
Source dataset
uspto-grants-1976_08
Patent number
US03976773

Reaction notes

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