Dichloroacetic Acid → HCID 69688412, compound

HRID 651194Notes

Reaction equation

HRID 651194 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@@H:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9]([N:11]1[CH2:14][CH:13]([OH:15])[CH2:12]1)=[O:10])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.ClC(Cl)C(O)=O>C1(C)C=CC=CC=1.CS(C)=O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:23])[NH:7][C@@H:8]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:9](=[O:10])[N:11]1[CH2:14][C:13](=[O:15])[CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 6597Dichloroacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69687358HCID 69687358, compound

Product 1

HCID 69688412HCID 69688412, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

[(1S)-Benzyl-2-(3-hydroxy-azetidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (320 mg, 1 mmol) was added in one portion to a mixture of 1-(3-dimethylaminopropyl)3-ethylcarbodiimide hydrochloride (DEC, 575 mg, 3 mmol) and dichloroacetic acid (192 mg, 1.5 mmol) in anhydrous toluene (2 mL) and anhydrous dimethylsulfoxide (2 mL). The mixture was stirred at 0-20° C. for 1 h, diluted with ethyl acetate, the resulting solution washed twice with 1N HCl, twice with saturated aqueous NaHCO3, dried and concentrated giving a colorless solid (304 mg, 96%).

Workup

  1. washthe resulting solution washed twice with 1N HCl, twice with saturated aqueous NaHCO3
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c1fc7a183001438da5b161d31b7be397
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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