1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 15546845, compound

HRID 1107597Notes

Reaction equation

HRID 1107597 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.CN.C[CH2:18][N:19]=C=NCCCN(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:18][NH:19][C:11](=[O:13])[CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 6364545Methylamine hydrochloride

Product 1

HCID 15546845HCID 15546845, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

BOC-β-alanine (0.50 g, 2.64 mmol) was dissolved in 4 mL DMF. Methylamine hydrochloride (198 mg, 2.93 mmol) and DMAP (427.2 mg, 3.50 mmol) were added, followed by EDCI (1.06 g, 5.53 mmol). After stirring at room temperature for 2 days the solvent was removed in a stream of nitrogen and the residue dried in vacuo. It was dissolved in 5 mL 1 M HCl, and the solution was extracted five times with ethyl acetate. The combined organic extracts were dried over MgSO4 and concentrated to yield 0.43 g (2.13 mmol, 81%) of BOC-β-alanine methylamide (14) as a white solid. mp. 117-118° C., 1H-NMR (300 MHz, CDCl3) δ 5.78 (b, NH), 5.15 (b, NH), 3.38 (q, J=6.1 Hz, 2 H), 2.78 (d, J=4.8 Hz, 3 H), 2.36 (t, J=6.1 Hz, 2 H), 1.40 (s, 9 H) 13C-NMR (75.5 MHz, CDCl3) δ 171.74 (C), 79.15 (C), 36.41 (CH2), 36.03 (CH2), 28.17 (3 CH3), 26.04 (CH3). ##STR27##

Workup

  1. customwas removed in a stream of nitrogen
  2. customthe residue dried in vacuo
  3. dissolutionIt was dissolved in 5 mL 1 M HCl
  4. extractionthe solution was extracted five times with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-25d9d840e8ab4ea9ba9c85c86bfb0ed8
Source dataset
uspto-grants-2000_05
Patent number
US06060585

Reaction notes

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