Diisopropylethylamine → HCID 67972135, compound

HRID 1804612Notes

Reaction equation

CS(O[C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:7])(=O)=O.C(N(CC)C(C)C)(C)C.[N:23]1([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CS(C)=O.O>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C@@H:6]([N:26]1[CH2:25][CH2:24][N:23]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][CH2:27]1)[CH3:7]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 0.35 g (1.7 mmol) of the title compound from Step A above in 3.5 mL of anhydrous dimethyl sulfoxide was added 0.60 mL (3.5 mmol) of N,N-diisopropylethylamine followed by 0.49 g (2.6 mmol) of tert-butyl piperazine-1-carboxylate. The resulting mixture was heated to 80° C. for 3 h then cooled to ambient temperature. The reaction was diluted with water and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography eluting with a 0-100% ethyl acetate in hexanes gradient to afford the title compound as a yellow gum (0.38 g, 75% yield. LC-MS: m/z (ES) 292.4 (MH)+.

Workup

temperaturethen cooled to ambient temperature
extractionthe aqueous phase was extracted with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated to dryness in vacuo
customThe residue was purified by silica gel chromatography
washeluting with a 0-100% ethyl acetate in hexanes gradient

Sources & evidence

ORD record: ord-866c4905f10c4fbb8516fda965472f93
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354403B2

Reaction notes

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