Ethanol → HCID 58120261, compound

HRID 533382Notes

Reaction equation

HRID 533382 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C@@H:13]([OH:18])[CH2:14][O:15][CH2:16][CH3:17])[CH2:9]1)=O)(C)(C)C.[H-].[Na+].[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1F.CCO>CN(C=O)C.Cl>[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[O:18][C@H:13]([C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[CH2:14][O:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 123112Benzene, 2,4-dichloro-1-fluoro-HCID 66858889(S)-3-((R)-2-Ethoxy-1-hydroxyethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

Product 1

HCID 58120261HCID 58120261, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-3-((R)-2-Ethoxy-1-hydroxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester (25.0 mg, 96.4 μmol) was dissolved in DMF (200 μL). NaH (2776 μg, 115.7 mmol) was added and the mixture was stirred at room temperature for 15 minutes. 2,4-Dichloro-1-fluorobenzene (22.6 μL, 192.8 μmol) was added and the mixture was stirred at 70° C. for 3 hours. The mixture was concentrated then dissolved in 1.2M HCl in EtOH (1.0 mL, 1.2 mmol) and stirred overnight. The product was concentrated and purified by preparative HPLC (10-40%, 60 min, BDS) to yield the title compound as a mono-TFA salt oil (24.4 mg, 100% purity). MS m/z: [M+H]+ calcd for C14H19Cl2NO2, 304.08. found 304.0.

Workup

  1. stirringthe mixture was stirred at 70° C. for 3 hours
  2. concentrationThe mixture was concentrated
  3. stirringstirred overnight
  4. concentrationThe product was concentrated
  5. custompurified by preparative HPLC (10-40%, 60 min, BDS)

Sources & evidence

ORD record
ord-0526e86200c448ec9adbf4cdf6810bbb
Source dataset
uspto-grants-2014_10
Patent number
US08853255B2

Reaction notes

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