Triethylamine → HCID 66888311, compound

HRID 252422Notes

Reaction equation

HRID 252422 reaction equation
[CH3:1][CH:2]([S:4]([Cl:7])(=[O:6])=[O:5])[CH3:3].[NH2:8][CH2:9][CH:10]([CH:12]([NH:34]C(=O)OC(C)(C)C)[CH2:13][CH:14]([CH2:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:28])[CH:23]=[C:22]2[CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:15]([CH3:17])[CH3:16])[OH:11].C(N(CC)CC)C>ClCCl>[ClH:7].[NH2:34][CH:12]([CH2:13][CH:14]([CH2:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:28])[CH:23]=[C:22]2[CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:15]([CH3:16])[CH3:17])[CH:10]([OH:11])[CH2:9][NH:8][S:4]([CH:2]([CH3:3])[CH3:1])(=[O:6])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 86618888HCID 86618888, compound

Product 1

HCID 66888311HCID 66888311, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.007 ml of propane-2-sulphonyl chloride is added to a solution of 0.026 g of tert-butyl {1-(2-amino -1-hydroxyethyl)-3-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-ylmethyl]-4-methylpentyl}carbamate (Example 3Kb), and 0.007 ml of triethylamine in 1 ml of dichloromethane is added at 0° C. After 6 hours, the reaction mixture is concentrated by evaporation—the N-Boc intermediate is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F). The N-Boc intermediate is dissolved in 0.82 ml of 4N HCl/dioxane—after 4 hours, the reaction mixture is concentrated by evaporation, and the residue is dissolved in 0.5 ml of tert-butanol, frozen in liquid nitrogen and lyophilized under high vacuum overnight. The title compound is identified on the basis of the Rf value from the residue.

Workup

  1. additionis added at 0° C
  2. concentrationthe reaction mixture is concentrated by evaporation—the N-Boc intermediate
  3. dissolutionThe N-Boc intermediate is dissolved in 0.82 ml of 4N HCl/dioxane—after 4 hours
  4. concentrationthe reaction mixture is concentrated by evaporation
  5. dissolutionthe residue is dissolved in 0.5 ml of tert-butanol
  6. temperaturefrozen in liquid nitrogen
  7. customlyophilized under high vacuum overnight

Sources & evidence

ORD record
ord-ff6f0484a4b343baa598defcefc5552d
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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