1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 2-(Boc-L-methionyl)-1-hydrazine carboxylate

HRID 2086249Notes

Reaction equation

HRID 2086249 reaction equation
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[NH:18][NH2:19].CCN=C=NCCCN(C)C>C(#N)C>[C:1]([NH:8][C@H:9]([C:14]([NH:19][NH:18][C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])[CH2:10][CH2:11][S:12][CH3:13])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 89857Boc-L-methionine

Product 1

HCID 20720845tert-butyl 2-(Boc-L-methionyl)-1-hydrazine carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of Boc-L-methionine (9.972 g) [Boc:tert-butoxycarbonyl] and tert-butyl carbazate (5.29 g) in acetonitrile (100 ml) was combined with WSC (9.202 g) and stirred at room temperature for 5 hours. The reaction mixture was concentrated and the resultant residue was combined with ethyl acetate and water, and the organic phase was washed with water, aqueous sodium bicarbonate and brine, dried and concentrated to obtain tert-butyl 2-(Boc-L-methionyl)-1-hydrazine carboxylate as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe organic phase was washed with water, aqueous sodium bicarbonate and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7e929feb42f04cdbaf60c1c851bef4c6
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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