1-Hydroxybenzotriazole → HCID 23560760, compound

HRID 1058414Notes

Reaction equation

HRID 1058414 reaction equation
ON1C2C=CC=CC=2N=N1.[Cl:11][C:12]1[CH:20]=[C:19]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][O:33][CH3:34])[CH:26]=2)=[O:22])[CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=O.[CH3:35][O:36][C:37](=[O:46])[CH:38]([P:40]([O:44][CH3:45])([O:42][CH3:43])=[O:41])[NH2:39]>CN(C)C=O>[CH3:35][O:36][C:37](=[O:46])[CH:38]([P:40]([O:42][CH3:43])([O:44][CH3:45])=[O:41])[NH:39][C:14](=[O:16])[C:13]1[CH:17]=[CH:18][C:19]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][O:33][CH3:34])[CH:26]=2)=[O:22])=[CH:20][C:12]=1[Cl:11]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 11084793Methyl 2-amino-2-(dimethoxyphosphoryl)acetateHCID 18673004HCID 18673004, compound

Product 1

HCID 23560760HCID 23560760, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-dicyclohexylcarbodiimide (0.216 g, 1.05 mmol) and 1-hydroxybenzotriazole (0.027 g, 0.2 mol) were added to a solution of 2-chloro-4-[[(3-methoxymethoxybenzyl) amino]carbonyl]benzoic acid (Example 124; 0.34 g, 1.0 mmol) and rac.-2-(dimethoxyphosphinyl)glycine methyl ester (Example 125; 197 mg, 1.0 mmol) in N,N-dimethylformamide (5 mL). The solution was stirred for 12 h, then was filtered and diluted with ethyl acetate. The resulting solution was washed with water, dried (Na2SO4), evaporated and the residual material was chromatographed (50-80% ethyl acetate/hexanes) to give rac.-N-[2-chloro-4-[[(3-methoxymethoxybenzyl) amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (0.24 g, 45% yield).

Workup

  1. filtrationwas filtered
  2. additiondiluted with ethyl acetate
  3. washThe resulting solution was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customthe residual material was chromatographed (50-80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-be3473fbeb294ce188e4e69c40f2c5d5
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

Loading…