Acetohydrazide → HCID 71205495, compound

HRID 1773091Notes

Reaction equation

HRID 1773091 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[CH2:10][CH2:11][C@H:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([NH:28][NH2:29])(=O)[CH3:26]>O1CCCC1>[CH2:1]([O:8][C:9](=[O:24])[CH2:10][CH2:11][C@H:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13]1[O:15][C:25]([CH3:26])=[N:28][N:29]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 83589L-Glutamic acid, N-((1,1-dimethylethoxy)carbonyl)-, 5-(phenylmethyl) ester

Product 1

HCID 71205495HCID 71205495, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

674 mg (2 mmol) of (S)-5-(benzyloxy)-2-(tert-butoxycarbonylamino)-5-oxopentanoic acid (Boc-Glu (OBzl)-OH) and 148 mg (2 mmol) of acetohydrazide were added with 5 ml of tetrahydrofuran, added with 356 mg of N,N-carbonyl diimidazole and stirred at room temperature overnight. The solvent was distilled away, and the resultant was purified using purified purification step A to obtain a crude purified substance of (4S)-4-(N′-acetylhydrazinecarbonyl)-4-{[(tert-butoxy)carbonyl]amino}butanoic acid benzyl ester. The obtained crude purified substance was dissolved in 2 ml of methylene chloride, which was added with 72 mg of Burgess reagent and stirred at room temperature overnight. Another 72 mg of Burgess reagent was added and stirred for two days. After distilling the solvent away, purification was carried out using purification step A to obtain the title compound.

Workup

  1. distillationThe solvent was distilled away
  2. customthe resultant was purified
  3. customusing purified
  4. custompurification step A
  5. customto obtain a crude
  6. custompurified substance of (4S)-4-(N′-acetylhydrazinecarbonyl)-4-{[(tert-butoxy)carbonyl]amino}butanoic acid benzyl ester
  7. customThe obtained crude
  8. custompurified substance
  9. dissolutionwas dissolved in 2 ml of methylene chloride
  10. additionwhich was added with 72 mg of Burgess reagent
  11. stirringstirred at room temperature overnight
  12. additionAnother 72 mg of Burgess reagent was added
  13. stirringstirred for two days
  14. distillationAfter distilling the solvent away
  15. custompurification
  16. custompurification step A

Sources & evidence

ORD record
ord-71d2dd625c2f47af9e9e3eacf43f1a03
Source dataset
uspto-grants-2016_02
Patent number
US09253997B2

Reaction notes

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