Acetylglycine → HCID 60646216, compound

HRID 400541Notes

Reaction equation

HRID 400541 reaction equation
[C:1]([NH:4][CH2:5][C:6]([OH:8])=O)(=[O:3])[CH3:2].CCN=C=[N:13][CH2:14][CH2:15][CH2:16]N(C)C.Cl.C(N)C#C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([NH:4][CH2:5][C:6]([NH:13][CH2:14][C:15]#[CH:16])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 10972AcetylglycineHCID 239041PropargylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 60646216HCID 60646216, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-acetylglycine (200 mg, 1.71 mmol), DMAP (11 mg, 0.09 mmol) and EDC hydrochloride (360 mg, 1.88 mmol) in DCM (10 mL) was added propargylamine (109 μL, 1.71 mmol). The reaction mixture was stirred at RT overnight and then evaporated in vacuo. The residue was purified by flash column chromatography, eluting with 0 to 5% methanol in DCM, to afford the title compound (12) (218 mg, 83%) as a white solid: 1H NMR (500 MHz, CDCl3) δ: 2.07 (3H, s), 2.25 (1H, t), 3.95 (2H, d), 4.07 (2H, dd), 6.34 (1H, br s), 6.49 (1H, b s).

Workup

  1. customevaporated in vacuo
  2. customThe residue was purified by flash column chromatography
  3. washeluting with 0 to 5% methanol in DCM

Sources & evidence

ORD record
ord-6b94b1efc0714b38abf5703ea2191f20
Source dataset
uspto-grants-2014_06
Patent number
US08741909B2

Reaction notes

Loading…