1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86641001, compound

HRID 1776974Notes

Reaction equation

HRID 1776974 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:12][CH2:13][CH2:14][CH2:15][C:16](O)=[O:17].CCN=C=NCCCN(C)C>C(Cl)Cl>[Br:12][CH2:13][CH2:14][CH2:15][C:16]([O:11][CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])=[O:17]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 758094-Bromobutyric acidHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 86641001HCID 86641001, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N-Boc-ethanolamine (2.10 g; 13.0 mmol), 4-Bromobutyric acid (2.18 g; 13.0 mmol) and N,N-dimethylaminopyridine (0.318 g; 2.60 mmol) were dissolved in CH2Cl2 (35 mL) and the mixture was cooled to 0° C.; EDAC (3.75 g; 13.6 mmol) was added and the reaction was slowly warmed to room temperature and stirred for 18 hours. Then the mixture was diluted with CH2Cl2, washed with aqueous Na2HPO4 (5%, 2×50 ml) aqueous NaH2PO4, (5%, 2×50 ml) and brine (1×40 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure.

Workup

  1. temperaturethe reaction was slowly warmed to room temperature
  2. washwashed with aqueous Na2HPO4 (5%, 2×50 ml) aqueous NaH2PO4, (5%, 2×50 ml) and brine (1×40 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a2663b165fc842ac9408bae12571a6dc
Source dataset
uspto-grants-2016_02
Patent number
US09266820B2

Reaction notes

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