Methoxyacetic Acid → HCID 178496364, compound

HRID 558272Notes

Reaction equation

HRID 558272 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-8d3c8cfd948d4e00bd987e2374271a8b
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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