4-Methylmorpholine → HCID 89725862, compound

HRID 592068Notes

Reaction equation

HRID 592068 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)=[O:2].CN(C([O:19]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>CN(C=O)C>[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:37][CH2:38][C:39]([O:40][CH2:41][CH3:42])=[O:19])=[O:8])=[O:2]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 120773-CarboxybenzaldehydeHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 89725862HCID 89725862, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-formylbenzoic acid 20 (0.1 g, 0.819 mmol) in DMF (2 mL) were added glysine ethyl ester (0.13 g, 0.98 mmol), HATU (0.37 g, 0.98 mmol), and NMM (0.2 g, (2.04 mmol). The reaction mixture was stirred at RT for 16 h. The reaction was monitored by LCMS. The reaction mixture was concentrated and column chromatographed to afford ethyl 2-(3-formylbenzamido)acetate 35 (146 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customcolumn chromatographed

Sources & evidence

ORD record
ord-4eaa5873bafc4b92a432e5ffa925db2b
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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