Ethylamine → (3-Ethylcarbamoyl-propyl)-carbamic acid tert-butyl ester

HRID 1726445Notes

Reaction equation

HRID 1726445 reaction equation
[CH2:1]([NH2:3])[CH3:2].[C:4]([NH:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]>C(Cl)Cl>[C:7]([O:6][C:4](=[O:5])[NH:11][CH2:12][CH2:13][CH2:14][C:15](=[O:17])[NH:3][CH2:1][CH3:2])([CH3:8])([CH3:9])[CH3:10]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acid

Product 1

HCID 11138962(3-Ethylcarbamoyl-propyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An aqueous solution of ethylamine (70%, 41 ml) was added into an ice cold solution of benzotriazole derivative 2 (50 g, 156 mmol) in CH2Cl2 (500 ml), stirred for 1 h at room temperature, diluted 2 times with CH2Cl2, washed with H2O, then brine, dried (Na2SO4), concentrated and dried in vacuo. Yield 32.845 g (91%). mp: 82-83° C. 1H NMR (CDCl3): 1.15 (t, J=7.27, 3H), 1.44 (s, 9H), 1.75-1.85 (m, 2H), 2.20 (t, J=7.10, 2H), 3.17 (q, J=6.49, 2H), 3.24-3.34 (m, 2H), 4.82 (s, 1H), 6.13 (bs, 1H). 13C NMR (CDCl3): 14.72, 24.91, 26.33, 28.35, 33.66, 33.92, 34.32, 39.78, 79.21, 156.44, 172.43. ESI-MS: 483.4 (M2Na+), 461.4 (M2H+), 321.2 (MH+).

Workup

  1. washwashed with H2O
  2. dry with materialbrine, dried (Na2SO4)
  3. concentrationconcentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ba06657bbcde4546a94abebaf096ac99
Source dataset
uspto-grants-2009_02
Patent number
US07491849B2

Reaction notes

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