Triethylamine → HCID 86618880, compound

HRID 252398Notes

Reaction equation

HRID 252398 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][CH:10]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:11][CH:12]([CH2:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH3:26])[CH:21]=[C:20]2[CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:13]([CH3:15])[CH3:14]>CS(C)=O.ClCCl>[CH:9]([CH:10]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:38])[CH3:37])[CH2:11][CH:12]([CH2:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH3:26])[CH:21]=[C:20]2[CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:13]([CH3:14])[CH3:15])=[O:8]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86618881HCID 86618881, compound

Product 1

HCID 86618880HCID 86618880, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

1.27 ml of triethylamine and then (over 20 minutes) a solution of 1.60 g of sulphur trioxide-pyridine complex in 6 ml of dimethyl sulphoxide are added dropwise at 0° C. to the solution of 1.44 g of tert-butyl {1-hydroxymethyl-3-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-ylmethyl]-4-methylpentyl}carbamate in 10 ml of dichloromethane. After 40 minutes, 10 ml of ice-water are added dropwise and the reaction mixture is stirred at 10° C. for a further 10 minutes. The reaction mixture is extracted with dichloromethane (3×)—the combined organic phases are washed successively with 10% aqueous sodium hydrogensulphate solution, water, 10% sodium hydrogencarbonate solution and brine, dried over magnesium sulphate and concentrated by evaporation. The crude title compound is obtained as a yellowish foam from the residue. Rf=0.73 (2:1 EtOAc-heptane). Rt=5.48 (gradient I).

Workup

  1. extractionThe reaction mixture is extracted with dichloromethane (3×)—the combined organic phases
  2. washare washed successively with 10% aqueous sodium hydrogensulphate solution, water, 10% sodium hydrogencarbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-caf0ccdbc0b94500a5dcea3bdd10ed88
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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