Diisopropylethylamine → HCID 178485964, compound

HRID 25633Notes

Reaction equation

HRID 25633 reaction equation
FC(F)(F)C(O)=O.[CH3:8][NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]#[C:17][CH2:18][O:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:12][CH2:11]1.[CH:24]1[C:29]([O:30][C:31](Cl)=[O:32])=[CH:28][CH:27]=[C:26]([Cl:34])[CH:25]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.OS([O-])(=O)=O.[K+].CCOCC>[Cl:34][C:26]1[CH:27]=[CH:28][C:29]([O:30][C:31]([N:9]([CH3:8])[C@H:10]2[CH2:11][CH2:12][C@H:13]([C:16]#[C:17][CH2:18][O:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:14][CH2:15]2)=[O:32])=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 178484804HCID 178484804, compound

Product 1

HCID 178485964HCID 178485964, compoundYield 117.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 86584777KHSO4 etherSolvent

Procedure

A solution of 1.41 g (corresponds to 3.0 mmol) of trans-Methanesulfonic acid 3-(4-methylamino-cyclohexyl)-prop-2-ynyl ester trifluoroacetate in 20 ml CH2Cl2 was first cooled at 0° C., treated with 0.5 ml (3.6 mmol) 4-chlorophenylchloroformate and then with 2.57 ml (15 mmol; 5 equivalents) of Huenig's base (during 3 min). After 45 min at RT, the mixture was dissolved in aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried over Na2SO4 and evaporated to give 1.41 g (quantitative) of crude trans-Methanesulfonic acid 3-{4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl}-prop-2-ynyl ester, MS: 400 (MH+, 1Cl). The crude product was directly used in the next step.

Workup

  1. washThe organic phases were washed with aqueous 10% NaCl
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-3791fd8ca8394af482791b3a75dbf5c8
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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