1,1'-Carbonyldiimidazole → HCID 59280003, compound

HRID 1875372Notes

Reaction equation

HRID 1875372 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[CH3:13][C:14]([CH3:20])([CH2:17][CH:18]=[CH2:19])[CH2:15][OH:16].Cl.[NH2:22][C@@H:23]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:24]([O:26][CH3:27])=[O:25]>CN(C=O)C>[CH:28]1([C@H:23]([NH:22][C:6]([O:16][CH2:15][C:14]([CH3:20])([CH3:13])[CH2:17][CH:18]=[CH2:19])=[O:7])[C:24]([O:26][CH3:27])=[O:25])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 107491582,2-Dimethylpent-4-en-1-olHCID 17747951Methyl (2S)-amino(cyclohexyl)acetate--hydrogen chloride (1/1)

Product 1

HCID 59280003HCID 59280003, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

CDI (1.42 g, 8.76 mmol) was added to a solution of 2,2-dimethylpent-4-en-1-ol [Ref.: E. Alexander Hill et al., 46(6) J. Org. Chem. 1177-82 (1981).] (1.00 g, 8.76 mmol) in DMF (12 mL) cooled with a water bath. The mixture was stirred for 30 minutes at RT. Methyl (2S)-amino(cyclohexyl)acetate hydrochloride (1.82 g, 8.76 mmol) was then added, and the mixture was heated to 50° C. for 16 hours and then cooled to RT. The reaction mixture was partitioned between EtOAc and water/1N HCl. The organic layer was extracted with water (3×) and brine. The organic layer was then dried over MgSO4, filtered and concentrated. The crude material was purified on silica gel (gradient elution, 0-10% EtOAc/hexane) to yield the title product (2.04 g, 75% yield). LRMS ESI+ (M+H)+ 312.5.

Workup

  1. temperaturecooled with a water bath
  2. temperaturethe mixture was heated to 50° C. for 16 hours
  3. temperaturecooled to RT
  4. customThe reaction mixture was partitioned between EtOAc and water/1N HCl
  5. extractionThe organic layer was extracted with water (3×) and brine
  6. dry with materialThe organic layer was then dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified on silica gel (gradient elution, 0-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-fa4db807d53d40d89f8d7536d9d66e57
Source dataset
uspto-grants-2012_11
Patent number
US08309540B2

Reaction notes

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