Dichloromethane → HCID 67426229, compound

HRID 1951911Notes

Reaction equation

HRID 1951911 reaction equation
Cl.[NH2:2][C@@H:3]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ClCCl.[CH:29]([C:31]1([NH:34][C:35](=[O:44])[O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:33][CH2:32]1)=O>C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH2:37]([O:36][C:35]([NH:34][C:31]1([CH2:29][NH:2][C@@H:3]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6])[CH2:33][CH2:32]1)=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 11600782D-Leucine Methyl Ester HydrochlorideHCID 54500481Benzyl (1-formylcyclopropyl)carbamate

Product 1

HCID 67426229HCID 67426229, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl D-leucinate hydrochloride (2.73 g, 15.1 mmol), zinc chloride (2.8 g, 20.5 mmol), and sodium triacetoxyborohydride (9.16 g, 41.1 mmol) were added to a dichloromethane (200 ml) solution of benzyl (1-formylcyclopropyl)carbamate (3.0 g, 13.7 mmol) and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, the residue obtained was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution and saturated brine and then the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=2:1 (v/v)] to give the title compound (2.24 g, 47%) as a pale yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue obtained
  3. washwashed with saturated aqueous sodium bicarbonate solution and saturated brine
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=2:1 (v/v)]

Sources & evidence

ORD record
ord-172bd77979f8483493de2ae9e2b43062
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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