Oxalyl chloride → HCID 69642585, compound

HRID 2215835Notes

Reaction equation

HRID 2215835 reaction equation
[C:1]([N:4]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][CH:18]=[CH:17]2)[CH2:5][CH2:6][O:7][C:8](=[O:10])[CH3:9])(=[O:3])[CH3:2].[C:21](Cl)(=[O:25])[C:22](Cl)=[O:23].[CH3:27][O-:28].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[CH3:27][O:28][C:21](=[O:25])[C:22]([C:17]1[C:16]2[C:20](=[C:12]([CH2:11][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6][OH:7])[CH:13]=[CH:14][CH:15]=2)[NH:19][CH:18]=1)=[O:23].[CH3:27][O:28][C:21](=[O:25])[C:22]([C:17]1[C:16]2[C:20](=[C:12]([CH2:11][N:4]([CH2:5][CH2:6][O:7][C:8](=[O:10])[CH3:9])[C:1](=[O:3])[CH3:2])[CH:13]=[CH:14][CH:15]=2)[NH:19][CH:18]=1)=[O:23]

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 10942334Sodium MethoxideHCID 69642345HCID 69642345, compound

Product 2

HCID 69642490HCID 69642490, compoundYield 20%HCID 69642585HCID 69642585, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of acetic acid 2-[acetyl-(1H-indol-7-ylmethyl)-amino]-ethyl ester (4.76 g, 17.36 mmol) in CH2Cl2 (100 ml) was cooled to 0° C. Oxalyl chloride (3.27 g, 26.04 mmol) was added and the reaction was warmed to room temperature. Upon completion, the reaction was cooled to −78° C. and sodium methoxide (4.14 mmol, 18.1 mmol, 25% w/v in methanol) was added. The solution was warmed to 20–24° C., and the mixture was diluted with ethyl acetate (400 mL), washed with saturated aqueous NaHCO3, brine, dried (MgSO4), filtered, and concentrated. SiO2 chromatography afforded the title compound (1.12 g, 20%) and (7-{[(2-Acetoxy-ethyl)-acetyl-amino]-methyl}-1H-indol-3-yl)-oxo-acetic acid methyl ester (3.0 g, 48%). MS (electrospray, m/z) 319.2 (M++1), 317.2 (M−−1).

Workup

  1. temperatureUpon completion, the reaction was cooled to −78° C.
  2. temperatureThe solution was warmed to 20–24° C.
  3. washwashed with saturated aqueous NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f78cdb3a739043a88f49d27cc5537fe8
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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