Diisopropylethylamine → HCID 89855305, compound

HRID 627176Notes

Reaction equation

[CH3:1][C:2]1[C@@H:3]([C:15]([OH:17])=O)[N:4]2[CH2:9][C@@H:7]([CH:8]=1)[N:6]([O:10][CH2:11][CH:12]=[CH2:13])[C:5]2=[O:14].[NH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(OCC)(=O)C.CN(C)C=O>[CH3:1][C:2]1[C@@H:3]([C:15]([NH:18][CH:19]2[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]2)=[O:17])[N:4]2[CH2:9][C@@H:7]([CH:8]=1)[N:6]([O:10][CH2:11][CH:12]=[CH2:13])[C:5]2=[O:14]

Participants

Conditions

Temperature: 25 °C

Procedure

Into a 100-mL round-bottom flask, was placed N,N-dimethylformamide (20 mL), crude of (2S,5R)-3-methyl-7-oxo-6-(prop-2-en-1-yloxy)-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxylic acid (Intermediate 150, 700 mg, 2.94 mmol, 1.00 equiv), tert-butyl 4-aminopiperidine-1-carboxylate (1.17 g, 5.84 mmol, 1.99 equiv), HATU (1.67 g, 4.39 mmol, 1.49 equiv), DIEA (1.51 g, 11.68 mmol, 3.98 equiv) at 0° C. The resulting solution was stirred for 12 h at 25° C. The resulting solution was diluted with 150 mL of ethyl acetate and it was washed with 3×100 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5-1:2). This resulted in 0.500 g (40%) of the title compound as a white solid.

Workup

customInto a 100-mL round-bottom flask, was placed
customat 0° C
washwas washed with 3×100 mL of brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-3810d98d83bd4d0b9087c273177f5f77
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309245B2

Reaction notes

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