Hydrazine hydrate (1:1) → Ser(tBu)-Thr(tBu)-NH-NH2

HRID 971541Notes

Reaction equation

HRID 971541 reaction equation
[NH2:1][C@H:2]([C:9]([NH:11][C@H:12]([C:20]([O:22]C)=O)[C@@H:13]([CH3:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:10])[CH2:3][O:4][C:5]([CH3:8])([CH3:7])[CH3:6].O.[NH2:25][NH2:26]>CO.C(OCC)(=O)C>[NH2:1][C@H:2]([C:9]([NH:11][C@H:12]([C:20]([NH:25][NH2:26])=[O:22])[C@@H:13]([CH3:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:10])[CH2:3][O:4][C:5]([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 131709964Ser(tBu)-Thr(tBu)-OMe

Product 1

HCID 131709965Ser(tBu)-Thr(tBu)-NH-NH2

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.253 g (7.4 mmols) of DPC-Ser(tBu)-Thr(tBu)-OMe in 18 ml of methanol are mixed with 5.55 ml (about 110 mmols) of hydrazine hydrate and left to stand for 10 hours at room temperature and 2 hours at 40° C. The reaction solution is taken up in 450 ml of ethyl acetate and washed four times with half-saturated sodium chloride solution. The solution is dried over sodium sulphate, concentrated to about 15 ml, and mixed with about 5 ml of petroleum ether. Overnight 3.17 g of a hydrazide of melting point 132°-134° C. crystallise out.

Workup

  1. waitleft
  2. washwashed four times with half-saturated sodium chloride solution
  3. dry with materialThe solution is dried over sodium sulphate
  4. concentrationconcentrated to about 15 ml
  5. additionmixed with about 5 ml of petroleum ether
  6. customOvernight 3.17 g of a hydrazide of melting point 132°-134° C. crystallise out

Sources & evidence

ORD record
ord-1fc1eda062084d8e9d0ac7d1f884fd4d
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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