4-Methylmorpholine → HCID 131726982, compound

HRID 2217380Notes

Reaction equation

[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].CN1CCOCC1.[C:26]([C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1)#[N:27]>C1COCC1>[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[C:26]([C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH-:33])=[CH:30][CH:29]=1)#[N:27]

Participants

Conditions

Temperature: -15 °C

Procedure

7.27 g (29.16 mmol) Z-Pro-OH and 3.2 ml (29.16 mmol) NMM were dissolved under stirring in 200 ml THF. Then the mixture was cooled to −15° C. and 3.79 ml (29.16 mmol) CKIBE were added. After about 10 minutes at −15° C., 4.24 g (32 mmol) 4-(cyano)benzylamine were added and stirring was continued for one hour at −15° C. and for another 12 hours at room temperature. The solvent was removed under vacuum; the residue was dissolved in 500 ml EE, and washed three times with 5% KHSO4 solution, one time with an NaCl-saturated solution, three times with an NaHCO3-saturated solution and three times with an NaCl-saturated solution, dried with Na2SO4 and concentrated in a vacuum.

Workup

addition3.79 ml (29.16 mmol) CKIBE were added
waitwas continued for one hour at −15° C. and for another 12 hours at room temperature
customThe solvent was removed under vacuum
dissolutionthe residue was dissolved in 500 ml EE
washwashed three times with 5% KHSO4 solution, one time with an NaCl-saturated solution, three times with an NaHCO3-saturated solution and three times with an NaCl-saturated solution
dry with materialdried with Na2SO4
concentrationconcentrated in a vacuum

Sources & evidence

ORD record: ord-9dea7dee344f44bcbfaff19df316fddc
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407982B2

Reaction notes

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