(2S)-2-Methyloxirane → HCID 86728139, compound

HRID 627677Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:4][O:3]1.[C:5]([O:9][C:10]([N:12]([C:20]1[C:25]([CH3:27])([CH3:26])[S:24](=[O:29])(=[O:28])[CH2:23][C@@:22]([CH2:40][F:41])([C:30]2[CH:35]=[C:34]([N+:36]([O-])=O)[CH:33]=[CH:32][C:31]=2F)[N:21]=1)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:11])([CH3:8])([CH3:7])[CH3:6]>>[NH2:36][C:34]1[CH:33]=[CH:32][C:31]2[O:3][C@@H:2]([CH3:1])[CH2:4][C@H:23]3[S:24](=[O:29])(=[O:28])[C:25]([CH3:27])([CH3:26])[C:20]([N:12]([C:10]([O:9][C:5]([CH3:7])([CH3:6])[CH3:8])=[O:11])[C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[N:21][C@:22]3([CH2:40][F:41])[C:30]=2[CH:35]=1

Participants

Reactant 2

HCID 146262(2S)-2-Methyloxirane

HCID 86728110HCID 86728110, compound

Product 1

HCID 86728139HCID 86728139, compoundYield 36.5%

Procedure

In an analogous sequence of reactions to that described in the preparation of trans intermediate 31, but using (S)-2-methyloxirane instead of 2,2-dimethyloxirane, tert-butyl N-tert-butoxycarbonyl-N-[(3S)-3-(fluoromethyl)-3-(2-fluoro-5-nitro-phenyl)-6,6-dimethyl-1,1-dioxo-2H-1,4-thiazin-5-yl]carbamate (preparation described in the synthesis of intermediate 22) was converted to the title compound (420 mg, 0.756 mmol, 36.5%) as a white foam. MS m/z=578.0 (M+Na).

Workup

custompreparation

Sources & evidence

ORD record: ord-c604f073e70047c9bd35854a5f1702ed
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309263B2

Reaction notes

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