Dichloroacetic Acid → HCID 54326710, compound

HRID 1872213Notes

Reaction equation

HRID 1872213 reaction equation
[CH2:1]([C@H:8]([NH:18][C:19]([C:21]1[NH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([Cl:30])=[CH:25][CH:24]=2)=[O:20])[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.ClC(Cl)C(O)=O>C1(C)C=CC=CC=1.CS(C)=O.C(OCC)(=O)C>[CH2:1]([C@H:8]([NH:18][C:19]([C:21]1[NH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([Cl:30])=[CH:25][CH:24]=2)=[O:20])[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][C:14](=[O:17])[CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 6597Dichloroacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10574415HCID 10574415, compound

Product 1

HCID 54326710HCID 54326710, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

5-Chloro-1H-indole-2-carboxylic acid [(1S)-benzyl-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-amide (Example 46, 669 mg) was added in one portion at 0° C. to a mixture of 1-(3-dimethylaminopropyl)3-ethylcarbodiimide hydrochloride (DEC, 1.80 g, 9.4 mmol) and dichloroacetic acid (307 mg, 1.5 mmol) in anhydrous toluene (e mL) and anhydrous dimethylsulfoxide (e mL). The mixture was stirred at 0-20° C. for 2 h, diluted with ethyl acetate, the resulting solution washed twice with 1 N HCl, twice with saturated aqueous NaHCO3, dried, concentrated and the residue purified by chromatography on silica gel eluted with 25%, 50%, and 75% ethyl acetate-hexanes giving a foam (424 mg, 64%).

Workup

  1. washthe resulting solution washed twice with 1 N HCl, twice with saturated aqueous NaHCO3
  2. customdried
  3. concentrationconcentrated
  4. customthe residue purified by chromatography on silica gel
  5. washeluted with 25%, 50%, and 75% ethyl acetate-hexanes giving a foam (424 mg, 64%)

Sources & evidence

ORD record
ord-ad917fdf812a4ca788a5542e9a59794e
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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