Diisopropylethylamine → HCID 178484025, compound

HRID 967219Notes

Reaction equation

HRID 967219 reaction equation
FC(F)(F)C(O)=O.[CH3:8][NH:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]#[C:18][CH2:19][O:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:13][CH2:12]1.[CH:25]1[C:30]([O:31][C:32](Cl)=[O:33])=[CH:29][CH:28]=[C:27]([Cl:35])[CH:26]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:35][C:27]1[CH:28]=[CH:29][C:30]([O:31][C:32]([N:9]([CH2:10][C@H:11]2[CH2:12][CH2:13][C@H:14]([C:17]#[C:18][CH2:19][O:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:15][CH2:16]2)[CH3:8])=[O:33])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 178484028HCID 178484028, compound

Product 1

HCID 178484025HCID 178484025, compoundYield 133%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7.70 g (corresponds to 9.63 mmol) of crude trans-methanesulfonic acid 3-(4-methylaminomethyl-cyclohexyl)-prop-2-ynyl ester trifluoro-acetate in 60 ml methylenechloride was treated at 0° C. with 1.61 ml (11.56 mmol) 4-chlorophenylchloroformate and then during 3 minutes with 8.25 ml (48.17 mmol; 5 equivalents) of Huenig's base. The reaction was stirred 45 hours at room temperature and extracted with aqueous 10% KHSO4/ether (3×). The organic phases were washed with aqueous 10% NaCl and dried over sodium sulfate to yield 5.3 g of crude trans-methanesulfonic acid 3-(4-{[(4-chloro-phenoxycarbonyl)-methyl-amino]-methyl}-cyclohexyl)-prop-2-ynyl ester as dark brown oil, MS: 414 (MH+, 1Cl).

Workup

  1. extractionextracted with aqueous 10% KHSO4/ether (3×)
  2. washThe organic phases were washed with aqueous 10% NaCl
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-4e574869a9204903b91a860211fbdf77
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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