Triethylamine → HCID 66952844, compound

HRID 2261053Notes

Reaction equation

HRID 2261053 reaction equation
N[C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@@H:3]1[C:15]([O:17][CH3:18])=[O:16].C(N(CC)CC)C.Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>C(Cl)Cl>[CH2:30]([O:29][C:27]([C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[C:15]([O:17][CH3:18])=[O:16])=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 58745510HCID 58745510, compound

Product 1

HCID 66952844HCID 66952844, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 257A (447 mg, 1.7 mmol) in CH2Cl2 (20 mL) was treated with triethylamine (0.3 mL, 2.2 mmol) followed by benzyl chloroformate (0.27 mL, 1.9 mmol) at room temperature. The reaction mixture was stirred for 18 hours, then washed with water (25 mL). The aqueous layer was extracted with CH2Cl2 (25 mL) and the combine organics were washed with saturated aqueous NaHCO3, 0.1N HCl, and brine. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to an oil. The crude material was purified by flash chromatography (30% EtOAc/hexanes) on silica gel to afford 411 mg (yield: 75%) of Compound 257B as an oil.

Workup

  1. washwashed with water (25 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (25 mL)
  3. washthe combine organics were washed with saturated aqueous NaHCO3, 0.1N HCl, and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to an oil
  7. customThe crude material was purified by flash chromatography (30% EtOAc/hexanes) on silica gel

Sources & evidence

ORD record
ord-b1cb724928374a5f9c9cadad61907d6a
Source dataset
uspto-grants-2010_12
Patent number
US07846931B2

Reaction notes

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