Triethylamine → HCID 68622419, compound

HRID 507852Notes

Reaction equation

HRID 507852 reaction equation
[CH3:1][CH:2]([S:4]([Cl:7])(=[O:6])=[O:5])[CH3:3].[NH2:8][CH2:9][C@@H:10]([C@@H:12]([NH:34]C(=O)OC(C)(C)C)[CH2:13][C@H:14]([CH2:18][NH:19][C:20](=[O:33])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:15]([CH3:17])[CH3:16])[OH:11].C(N(CC)CC)C>ClCCl>[ClH:7].[NH2:34][C@H:12]([C@@H:10]([OH:11])[CH2:9][NH:8][S:4]([CH:2]([CH3:3])[CH3:1])(=[O:6])=[O:5])[CH2:13][C@@H:14]([CH:15]([CH3:17])[CH3:16])[CH2:18][NH:19][C:20](=[O:33])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 69176508HCID 69176508, compound

Product 1

HCID 68622419HCID 68622419, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.007 ml of propane-2-sulphonyl chloride is added at 0° C. to a solution of 0.0255 g of tert-butyl (1(S)-(2-amino-1(S)-hydroxyethyl)-3(S)-{[2-(3-methoxypropoxy)benzoylamino]methyl}-4-methylpentyl)carbamate (Example 2b) and 0.007 ml of triethylamine in 1 ml of dichloromethane. After 6 hours, the reaction mixture is concentrated by evaporation—the N-Boc intermediate is identified from the residue by means of flash chromatography (SiO2 60F) on the basis of the Rf value. This 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 from the residue on the basis of the Rf value.

Workup

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

Sources & evidence

ORD record
ord-f7628f3d17044f2aaa4c2e92871a4f5e
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

Loading…