Hydrazine hydrate (1:1) → HCID 53905041, compound

HRID 1633273Notes

Reaction equation

HRID 1633273 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:32]([OH:34])=[O:33])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][N:21]2C(=O)C3=CC=CC=C3C2=O)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:32]([OH:34])=[O:33])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][CH2:20][NH2:21])=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53928720HCID 53928720, compound

Product 1

HCID 53905041HCID 53905041, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diphenylmethyl ester of N-tert-butoxycarbonyl-O-(3-phthalimidopropyl)-L-tyrosine (4.4 g) and hydrazine hydrate (0.52 g) in ethanol (50 ml) was heated under reflux for 2.5 hours. After cooling, the resulting precipitates were filtered off and the filtrate was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The extract was washed with water and brine, dried and evaporated to dryness to give diphenylmethyl ester of N-tert-butoxycarbonyl-O-(3-aminopropyl)-L-tyrosine (2.5 g) as oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. temperatureAfter cooling
  4. customthe resulting precipitates
  5. filtrationwere filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionThe residue was diluted with water
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with water and brine
  10. customdried
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-332daded63fb4be5b31f8ea18be40dd8
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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