Ammonia → HCID 86741163, compound

HRID 1249295Notes

Reaction equation

HRID 1249295 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][O:9][C:10](=[O:28])[C@H:11]([CH3:27])[N:12]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:13]2[CH:15](CCCCl)[CH2:14]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH3:31].[CH:32](O)([CH3:34])[CH3:33]>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10](=[O:28])[C@H:11]([CH2:27][CH2:33][CH2:32][CH2:34][NH2:31])[N:12]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH:13]2[CH2:15][CH2:14]2)=[CH:29][CH:30]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 3776IsopropanolHCID 86741164HCID 86741164, compound

Product 1

HCID 86741163HCID 86741163, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The cyclopropyl alanine derivative Boc 3-(3-Chloropropyl) cyclopropyl alanine p-nitrobenzyl Ester (16) is treated with a 1M solution of ammonia in isopropanol at 50° C. in a sealed pressure bottle for 48 hrs. Evaporation of the solution gives a solid residue which is dissolved in warm ethyl acetate (5 ml) and the solution is washed with saturated NaCl solution (3×25 ml) and dried over anhyd. Na2SO4. Evaporation of the solution gives Boc cyclopropyl lysine p-nitrobenzyl ester (17) which recrystallized from ethyl acetate-hexane. NMR (CDCl3) δ: 1.2-1.8 (m, 5H, CH2CH2CH), 0.8-1.1 (m, 2H, CH2), 2.5 (m, 2H, CH2NH2).

Workup

  1. customEvaporation of the solution
  2. customgives a solid residue which
  3. washthe solution is washed with saturated NaCl solution (3×25 ml)
  4. customdried over anhyd
  5. customEvaporation of the solution

Sources & evidence

ORD record
ord-1d3f771a0b9b4e079dd97cf18350f537
Source dataset
uspto-grants-1986_12
Patent number
US04629784

Reaction notes

Loading…