Dimethylformamide → Glycine, N-(2,1,3-benzoxadiazol-5-ylcarbonyl)-, methyl ester

HRID 1867523Notes

Reaction equation

HRID 1867523 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:2]=12.C1C=CC2N([OH:22])N=NC=2C=1.[CH3:23][CH2:24][N:25]=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.CN([CH:47]=[O:48])C>[Cl-].[Na+].O>[CH3:47][O:48][C:23](=[O:22])[CH2:24][NH:25][C:10]([C:7]1[CH:8]=[CH:9][C:2]2[C:3]([CH:6]=1)=[N:4][O:5][N:1]=2)=[O:12]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27354542,1,3-Benzoxadiazole-5-carboxylic acid

Product 1

HCID 14541753Glycine, N-(2,1,3-benzoxadiazol-5-ylcarbonyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

492 mg (3 mmol) benzo[1,2,5]oxadiazole-5-carboxylic acid 376 mg (1 eq.) glycine methyl ester hydrochloride, 486 mg (1.2 eq.) HOBt and 690 mg (1.2 eq.) EDC.HCl are dissolved in 20 mL DMF under argon and the reaction mixture is stirred at room temperature for 90 minutes after addition of 2 mL (4 eq.) Hünig's base. The reaction mixture is poured onto ice and brine, and extracted with ethyl acetate. The combined organic phases are dried with sodium sulfate and evaporated to yield the desired product as a beige powder. MS (ES+): 236 (M+1).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried with sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-73831c29fabb4e889fa55e328dcbdffe
Source dataset
uspto-grants-2009_12
Patent number
US07632851B2

Reaction notes

Loading…