Triethylamine → HCID 53956725, compound

HRID 1655005Notes

Reaction equation

HRID 1655005 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH3:15][O:16][C:17](=[O:21])[CH2:18][NH:19][CH3:20].C(N(CC)CC)C.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH3:15][O:16][C:17](=[O:21])[CH2:18][N:19]([C:11](=[O:13])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH3:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 158763-Nitrophenylacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)

Product 1

HCID 53956725HCID 53956725, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-nitrophenylacetic acid (25 g, 0.14 mol), sarcosine methyl ester hydrochloride (20.2 g, 0.15 mol), triethylamine (20 ml, 0.15 mol) and 4-dimethylaminopyridine (17.7 g, 0.15 mol) in dichloromethane (300 ml) was added, under nitrogen, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (27.8 g, 0.15 mol). The mixture was stirred at room temperature for 18 h then the solvent removed in vacuo. Ethyl acetate (300 ml) was added to the residue and the mixture partitioned with 1M HCl (2×200 ml), saturated sodium bicarbonate solution (2×200 ml), water (200 ml) and brine (200 ml). The organic phase was separated, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica gel, using petrol:ethyl acetate (1:1) as the eluant, to afford the title amide (25 g, 68%) as a yellow oil. 1H NMR (360MHz, CDCl3) δ3.13 (3H, s), 3.75 (3H, s), 3.88 (2H, s), 4.16 (2H, s), 7.26-7.65 (2H, m), 8.09-8.14 (2H, m). MS (CI, NH3), 284 (M+NH4+).

Workup

  1. customthe solvent removed in vacuo
  2. additionEthyl acetate (300 ml) was added to the residue
  3. customthe mixture partitioned with 1M HCl (2×200 ml), saturated sodium bicarbonate solution (2×200 ml), water (200 ml) and brine (200 ml)
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-3c676551655b40b0be3172ff9ef35d39
Source dataset
uspto-grants-1995_04
Patent number
US05410049

Reaction notes

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