Triethylamine → HCID 53837307, compound

HRID 1740749Notes

Reaction equation

HRID 1740749 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:19]2[CH:18]=[C:17]3[CH:20]([CH2:23][C:24]([OH:26])=O)[CH2:21][O:22][C:16]3=[CH:15][C:14]=2[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([N:29](CC)[CH2:30]C)C.ClC(OCC)=O>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[C:19]2[CH:18]=[C:17]3[CH:20]([CH2:23][C:24]([N:29]([CH3:30])[CH3:27])=[O:26])[CH2:21][O:22][C:16]3=[CH:15][C:14]=2[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 21833027HCID 21833027, compound

Product 1

HCID 53837307HCID 53837307, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(Benzyloxycarbonyl)-2,3,6,7-tetrahydrofuro[2,3-f]indol-3-ylacetic acid (D22, 0.89 g, 2.5 mmol) and triethylamine (0.7 ml, 5 mmol) were stirred in dichloromethane (80 ml) under Ar at 0° C. as ethyl chloroformate (0.27 ml, 92.8 mmol) was added. The mixture was stirred for 2 h, and dimethylamine gas was then bubbled through the solution for 10 min. It was then washed with water, K2CO3 solution and brine, dried (Na2SO4) and evaporated. Chromatography of the crude product on silica, eluting with 75% ethyl acetate/petroleum ether (b.p. 60-80° C.) gave the title compound (0.44 g, 46%) as an off-white solid.

Workup

  1. additionwas added
  2. customdimethylamine gas was then bubbled through the solution for 10 min
  3. washIt was then washed with water, K2CO3 solution and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. washChromatography of the crude product on silica, eluting with 75% ethyl acetate/petroleum ether (b.p. 60-80° C.)

Sources & evidence

ORD record
ord-a64c65e3d1014c08a3d56fa77991aced
Source dataset
uspto-grants-1999_10
Patent number
US05972935

Reaction notes

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