Methoxyacetic Acid → HCID 178496364, compound

HRID 2215315Notes

Reaction equation

HRID 2215315 reaction equation
C(N=C=NC1CCCCC1)C1C=CC=CC=1.[CH3:17][O:18][CH2:19][C:20]([OH:22])=O.[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([O:32][C:33]2[C:34]([CH3:45])=[N:35][NH:36][C:37]=2[CH2:38][N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH:31]=1)[C:27]#[N:28]>ClCCl>[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([O:32][C:33]2[C:34]([CH3:45])=[N:35][NH:36][C:37]=2[CH2:38][N:39]2[CH2:40][CH2:41][N:42]([C:20](=[O:22])[CH2:19][O:18][CH3:17])[CH2:43][CH2:44]2)[CH:31]=1)[C:27]#[N:28]

Participants

5

Reactant 3

HCID 12251Methoxyacetic AcidHCID 5067457N-benzyl-N'-cyclohexylcarbodiimideHCID 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-643d7a5820e24c38bed1a3df005fbe91
Source dataset
uspto-grants-2006_09
Patent number
US07109228B2

Reaction notes

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