N,N'-Dimethylethylenediamine → (S)-methyl-3-(5'-fluoro-2,2-dimethyl-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)-5-(2-oxooxazolidin-3-yl)benzoate

HRID 1805361Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C@@:5]12[CH2:13][C:12]1([CH3:15])[CH3:14].[CH3:16][O:17][C:18](=[O:32])[C:19]1[CH:24]=[C:23]([N:25]2[CH2:29][CH2:28][O:27][C:26]2=[O:30])[CH:22]=[C:21](Br)[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>C(#N)C.[Cu]I>[CH3:16][O:17][C:18](=[O:32])[C:19]1[CH:24]=[C:23]([N:25]2[CH2:29][CH2:28][O:27][C:26]2=[O:30])[CH:22]=[C:21]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[C@@:5]3([CH2:13][C:12]3([CH3:15])[CH3:14])[C:6]2=[O:11])[CH:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A suspension of (R) and (S)-5′-fluoro-2,2-dimethylspiro[cyclopropane-1,3′-indolin]-2′-one (2 mmol) (prepared as in Example 100), methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoate (682 mg, 2 mmol), CuI (76 mg, 0.4 mmol), potassium carbonate (545 mg, 4 mmol) and N,N′-dimethyl-ethane-1,2-diamine (86 uL, 0.8 mmol) in acetonitrile (15 mL) was stirred for 16 hours at 90° C. The precipitate was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford the title compound as white powder (480 mg, 80%) which was used for the next step without further purification.

Workup

filtrationThe precipitate was filtered off
washwashed with ethyl acetate
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-a45b143ce03e4bbd95ca59db818facf5
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354443B2

Reaction notes

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