4-Methylmorpholine → HCID 10435474, compound

HRID 1392091Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:8][CH:7]=[CH:6][C@@H:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]([CH2:15][CH2:16][O:17][CH3:18])[C:3]1=[O:19].[F:20][C:21]1[CH:22]=[C:23]([CH2:28][C:29]([NH:31][C@H:32]([C:34](O)=[O:35])[CH3:33])=[O:30])[CH:24]=[C:25]([F:27])[CH:26]=1.CCN=C=NCCCN(C)C.Cl.CN1CCOCC1>C(Cl)Cl>[F:20][C:21]1[CH:22]=[C:23]([CH2:28][C:29]([NH:31][C@H:32]([C:34]([NH:1][C@H:2]2[CH2:8][CH:7]=[CH:6][C@@H:5]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:4]([CH2:15][CH2:16][O:17][CH3:18])[C:3]2=[O:19])=[O:35])[CH3:33])=[O:30])[CH:24]=[C:25]([F:27])[CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (3S,7S)-3-amino-1-(2-methoxyethyl)-7-phenyl-1,3,4,7-tetrahydro-2H-azepin-2-one (6d) (55 mg) in DCM (4 mL) at 0° C. under N2 was added N-[(3,5-difluorophenyl)acetyl]-L-alanine (51 mg), HOBt-hydrate (71 mg), EDAC.HCl (61 mg) and N-methyl morpholine (34 mg). The reaction mixture was stirred 1 h at 0° C. and 3 h at RT, then diluted with 30% hexanes/EtOAc (100 mL). The organic phase was consecutively washed with H2O, 0.2 N HCl, saturated NaHCO3, and brine, dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography (1%-2% MeOH/DCM) to afford a white solid (82 mg, 80%).

Workup

washThe organic phase was consecutively washed with H2O, 0.2 N HCl, saturated NaHCO3, and brine
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated
customThe crude product was purified by flash chromatography (1%-2% MeOH/DCM)

Sources & evidence

ORD record: ord-5bbf42c416644fbba99fe8ac96959a53
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342007B2

Reaction notes

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