Hydrochloric Acid → HCID 66616051, compound

HRID 2367060Notes

Reaction equation

HRID 2367060 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]1[CH2:15][CH2:14][C@H:13]([C:16]([OH:18])=[O:17])[CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].I[CH3:20].Cl>O1CCCC1.CN(C)C=O>[C:3]([O:7][C:8]([N:10]([CH3:20])[C@@H:11]1[CH2:15][CH2:14][C@H:13]([C:16]([OH:18])=[O:17])[CH2:12]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 1512529(1S,3R)-3-(((tert-butoxy)carbonyl)amino)cyclopentane-1-carboxylic acid

Product 1

HCID 66616051HCID 66616051, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of sodium hydride (89 mg, 2.24 mmol) in tetrahydrofuran (10 mL) and dimethyl formamide (10 mL) cooled in an ice bath was added (1S,3R)-3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid (427 mg, 1.86 mmol, WO2006/011035) and iodomethane (128 microL, 2.05 mmol). The mixture was allowed to warm to room temperature and stirred for 20 h. Sodium hydride (178 mg, 4.474 mmol) and idomethan (256 microL, 4.102 mmol) were added, and the reaction mixture was stirred at 20 h at room temperature. Reaction mixture was acidified to pH 3.5 with 1 mol/L hydrochloric acid and extracted with ethyl acetate. Organic layer was dried over sodium sulfate and concentrated under reduced pressure. Crude material was purified by column chromatography (50% ethyl acetate in hexane containing 1.5% acetic acid) to give the desired compound as a colorless solid (138.0 mg, 31%).

Workup

  1. temperaturecooled in an ice bath
  2. stirringthe reaction mixture was stirred at 20 h at room temperature
  3. customReaction mixture
  4. extractionextracted with ethyl acetate
  5. dry with materialOrganic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customCrude material was purified by column chromatography (50% ethyl acetate in hexane containing 1.5% acetic acid)

Sources & evidence

ORD record
ord-056d885c7ddc45f98f2ab18976e003dc
Source dataset
uspto-grants-2014_04
Patent number
US08697877B2

Reaction notes

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