Hydrazine hydrate (1:1) → Z-Lys(Boc)-Lys(Boc)-NHNH2

HRID 328756Notes

Reaction equation

HRID 328756 reaction equation
[NH:1]([C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[C@H:2]([C:15]([NH:17][C@H:18]([C:31](OC)=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].O.[NH2:46][NH2:47]>C(O)C>[NH:1]([C:35]([O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:36])[C@H:2]([C:15]([NH:17][C@H:18]([C:31]([NH:46][NH2:47])=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59070592Z-Lys(Boc)-Lys(Boc)-OMe

Product 1

HCID 131710715Z-Lys(Boc)-Lys(Boc)-NHNH2

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound XII (1.50 g, 2.4 mmoles) is dissolved in ethanol (10 ml) and hydrazine hydrate (1.16 ml, 24 mmoles) is added. The mixture is allowed to stand at room temperature for 24 hours and then evaporated in vacuo. The resulting solid residue is dissolved in water-saturated ethyl acetate and the solution is washed with water two times and quickly dried over magnesium sulfate. The crystalline precipitates which separated upon standing at room temperature are filtered off, washed with ether and dried in vacuo. Recrystallization from ethyl acetate-ether affords the hydrazide XIII in pure form; yield 1.41 g (94%), mp. 121°-123° C, [α]D22.5 - 8.5°±0.5° (c 1.0, dimethylformamide), -18.2°±0.6° (c 1.0, methanol).

Workup

  1. customevaporated in vacuo
  2. dissolutionThe resulting solid residue is dissolved in water-saturated ethyl acetate
  3. washthe solution is washed with water two times
  4. dry with materialquickly dried over magnesium sulfate
  5. customThe crystalline precipitates which
  6. customseparated
  7. customupon standing at room temperature
  8. filtrationare filtered off
  9. washwashed with ether
  10. customdried in vacuo
  11. customRecrystallization from ethyl acetate-ether

Sources & evidence

ORD record
ord-be41a4811a0c4c3ca303ae6d6b6a83a0
Source dataset
uspto-grants-1977_04
Patent number
US04018753

Reaction notes

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