Triethylamine → HCID 13561207, compound

HRID 1822809Notes

Reaction equation

HRID 1822809 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C[N:17](C)[CH2:18][CH2:19][CH2:20]N=C=NCC.C(N(CC)CC)C.C(N)C#C>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][C:12](=[O:14])[NH:17][CH2:18][C:19]#[CH:20])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 239041PropargylamineHCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 13561207HCID 13561207, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-tert-butoxycarbonylaminobutyric acid (5 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.66 g) and triethylamine (7.47 g) in dichloromethane (80 mL) at rt was added 2-propynylamine (1.49 g). After being stirred at rt for 3 h, the mixture was diluted with dichloromethane (80 mL) and washed with 0.5 M HCl (aqueous, 2×), saturated NaHCO)3 (1×) and water (1×). The dichloromethane was dried over sodium sulfate, filtered and evaporated to afford (3-Prop-2-ynylcarbamoyl-propyl)-carbamic acid tert-butyl ester (1.67 g).

Workup

  1. washwashed with 0.5 M HCl (aqueous, 2×), saturated NaHCO)3 (1×) and water (1×)
  2. dry with materialThe dichloromethane was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-8cab12d2546a4ba5a95d4a32a8f057cb
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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