Diisopropylethylamine → {[2-(Tert-butoxycarbonylamino)-ethyl]-methyl-amino}-acetic acid benzyl ester

HRID 910000

Reaction equation

HRID 910000 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:24])[CH2:21][NH:22][CH3:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:25]([O:29][C:30]([NH:32][CH2:33][CH2:34]Br)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:12]([O:19][C:20](=[O:24])[CH2:21][N:22]([CH2:34][CH2:33][NH:32][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[CH3:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 122108994-Methylbenzene-1-sulfonic acid--benzyl N-methylglycinate (1/1)

Product 1

HCID 59650730{[2-(Tert-butoxycarbonylamino)-ethyl]-methyl-amino}-acetic acid benzyl esterYield 38.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg (1.42 mmol) of sarcosine benzyl ester p-toluenesulfonate, 478 mg (2.13 mmol) of 2-(tert-butoxycarbonylamino)-ethyl bromide, and 0.25 mL (2.13 mmol) of diisopropyl-ethylamine were dissolved in methylene chloride (10 mL), and then stirred at room temperature for approximately three days. After completion of the reaction, the reaction solution was concentrated and the residue obtained was purified by silica gel column chromatography (ethyl acetate) to yield 175 mg (38%) of {[2-(tert-butoxycarbonylamino)-ethyl]-methyl-amino}-acetic acid benzyl ester as a colorless viscous oil.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated
  3. customthe residue obtained
  4. customwas purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-8aa04aed8f674ce49ce09455ac4e5e70
Source dataset
uspto-grants-2011_09
Patent number
US08022047B2

Linked notes

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