Methoxyacetic Acid → HCID 178496364, compound

HRID 2114636Notes

Reaction equation

HRID 2114636 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=O.[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([O:16][C:17]2[C:18]([CH3:29])=[N:19][NH:20][C:21]=2[CH2:22][N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:15]=1)[C:11]#[N:12]>ClCCl>[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([O:16][C:17]2[C:18]([CH3:29])=[N:19][NH:20][C:21]=2[CH2:22][N:23]2[CH2:24][CH2:25][N:26]([C:4](=[O:6])[CH2:3][O:2][CH3:1])[CH2:27][CH2:28]2)[CH:15]=1)[C:11]#[N:12]

Participants

4

Reactant 2

HCID 12251Methoxyacetic AcidHCID 178434619HCID 178434619, compound

Product 1

HCID 178496364HCID 178496364, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Benzyl-N-cyclohexylcarbodiimide polymer bound (624 mg of 1.3 mmol/g, 0.480 mmol) was added in one portion to a stirred solution of methoxyacetic acid (37 μL, 0.480 mmol) and the amine of Example 78 (80 mg, 0.240 mmol) in dichloromethane (5 ml) at room temperature under nitrogen. The reaction was stirred for 1 hour and the polymer bound reagent was removed by filtration. The filtrate was concentrated under reduced pressure and the crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:4:1, by volume) to provide the title compound (45 mg) as a white foam.

Workup

  1. customat room temperature
  2. customwas removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:4:1, by volume)

Sources & evidence

ORD record
ord-57854c21e5de40a1ab96b5fa26f9c487
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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