Trifluoroacetic acid → Trifluoroacetate

HRID 917582Notes

Reaction equation

HRID 917582 reaction equation
[Br:1][CH2:2][C:3]([NH:5][CH2:6][CH2:7][NH:8]C(OC(C)(C)C)=O)=[O:4].[C:16]([OH:22])([C:18]([F:21])([F:20])[F:19])=[O:17]>ClCCl>[Br:1][CH2:2][C:3]([NH:5][CH2:6][CH2:7][NH2:8])=[O:4].[F:19][C:18]([F:21])([F:20])[C:16]([O-:22])=[O:17]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 13502099tert-Butyl [2-(2-bromoacetamido)ethyl]carbamate

Product 2

HCID 84468TrifluoroacetateHCID 22027308HCID 22027308, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-bromoacetyl-N′-BOC-ethylenediamine (3) is dissolved in 50% TFA in dichloromethane (5 ml of the solution per mmol of 3) at 20° C. The deprotection is allowed to proceed for 30 min, then the reaction mixture is concentrated on a rotary evaporator and solidifies upon addition of dry ethyl ether. The solid material is filtered off, washed with ether/petroleum ether on filter and dried. The desired N-bromoacetyl-ethylenediamine is obtained in the form of triflouroacetate salt.

Workup

  1. concentrationthe reaction mixture is concentrated on a rotary evaporator
  2. additionsolidifies upon addition of dry ethyl ether
  3. filtrationThe solid material is filtered off
  4. washwashed with ether/petroleum ether
  5. filtrationon filter
  6. customdried

Sources & evidence

ORD record
ord-d8a26f2d03cc4a879de765154bf261fa
Source dataset
uspto-grants-2007_09
Patent number
US07273920B2

Reaction notes

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