Triethylamine → HCID 131728267, compound

HRID 499715Notes

Reaction equation

HRID 499715 reaction equation
[CH3:1][CH:2]([S:4]([Cl:7])(=[O:6])=[O:5])[CH3:3].[CH3:8][O:9][C:10](=[O:42])[NH:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:22](=[O:41])[CH2:23][C:24]([CH3:40])([CH3:39])[CH2:25][C@H:26]([NH:31]C(OC(C)(C)C)=O)[C@@H:27]([OH:30])[CH2:28][NH2:29])[CH2:13]1.C(N(CC)CC)C>ClCCl>[ClH:7].[CH3:8][O:9][C:10](=[O:42])[NH:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:22](=[O:41])[CH2:23][C:24]([CH3:40])([CH3:39])[CH2:25][C@H:26]([NH2:31])[C@@H:27]([OH:30])[CH2:28][NH:29][S:4]([CH:2]([CH3:3])[CH3:1])(=[O:6])=[O:5])[CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 69176521HCID 69176521, compound

Product 1

HCID 131728267HCID 131728267, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.007 ml Propan-2-sulfonyl chlorid are added to a solution of 0.026 g [1-(7-amino-5(S)-tert-butoxycarbonylamino-6(S)-hydroxy-3,3-dimethyl-heptanoyl)-1,2,3,4-tetrahydro-quinolin-3(R,S)-yl]-carbamic acid methyl ester (Example 18b) and 0.007 ml triethylamine in 1 ml dichlormethane at 0° C. After 5 hours, the reaction mixture is concentrated. The intermediate N-Boc derivative is identified from the residue by means of flash chromatography (SiO2 60 F) based on its Rf value. This is dissolved in 0.82 ml 4N HCl (in dioxane), stirred for 4 hours and concentrated. The residue is dissolved in 0.5 ml tert-butanol, frozen in liquid nitrogen and lyophilized to give the title compound which is identified from the residue based on its Rf value.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. dissolutionThis is dissolved in 0.82 ml 4N HCl (in dioxane)
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in 0.5 ml tert-butanol
  5. temperaturefrozen in liquid nitrogen

Sources & evidence

ORD record
ord-2f05b99be1d94bfa931aa9fbd5c2af02
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

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