Acetylglycine → HCID 60646216, compound

HRID 632920Notes

Reaction equation

HRID 632920 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-2e73a466970944a0aad2cbb49b3658f6
Source dataset
uspto-grants-2016_04
Patent number
US09321773B2

Reaction notes

Loading…