Carbamate → HCID 86728131, compound

HRID 627669Notes

Reaction equation

HRID 627669 reaction equation
C(=O)([O-])N.[C:5]([O:9][C:10]([N:12]([C:20]1[C:25]([CH3:27])([CH3:26])[S:24](=[O:29])(=[O:28])[C@@H:23]([CH2:30][C@@H:31]([OH:33])[CH3:32])[C@:22]([C:35]2[CH:40]=[C:39]([N+:41]([O-:43])=[O:42])[CH:38]=[CH:37][C:36]=2F)([CH3:34])[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].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[CH3:27][C:25]1([CH3:26])[S:24](=[O:29])(=[O:28])[C@@H:23]2[CH2:30][C@H:31]([CH3:32])[O:33][C:36]3[CH:37]=[CH:38][C:39]([N+:41]([O-:43])=[O:42])=[CH:40][C:35]=3[C@@:22]2([CH3:34])[N:21]=[C:20]1[N:12]([C:10]([O:9][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:11])[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 276CarbamateHCID 10796Cesium carbonateHCID 86728132HCID 86728132, compound

Product 1

HCID 86728131HCID 86728131, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of cis and trans isomers, tert-butyl N-tert-butoxycarbonyl-N-[2R,3R)-3-(2-fluoro-5-nitro-phenyl)-2-[(2S)-2-hydroxypropyl]-3,6,6-trimethyl-1,1-dioxo-2H-1,4-thiazin-5-yl]carbamate and tert-butyl N-tert-butoxycarbonyl-N-[(2S,3R)-3-(2-fluoro-5-nitro-phenyl)-2-[(2S)-2-hydroxypropyl]-3,6,6-trimethyl-1,1-dioxo-2H-1,4-thiazin-5-yl]carbamate (1.8 g, 3.06 mmol) and cesium carbonate (4.99 g, 15.32 mmol) were combined in DMSO (15 ml) and stirred at room temperature for 6 h. The solution was diluted with water and the precipitate was collected by filtration, washed with water, and dried under vacuum. The product was purified via silica gel column chromatography (80 g column) using 10-50% ethyl acetate in heptane to afford to afford tert-butyl N-[(4aR,6S,11bR)-3,3,6,11b-tetramethyl-10-nitro-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate (1.62 g, 2.85 mmol, 93% yield). MS m/z=590 [M+Na].

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water
  3. customdried under vacuum
  4. customThe product was purified via silica gel column chromatography (80 g column)
  5. customto afford

Sources & evidence

ORD record
ord-c0b7e587f29b4d649b724d7796a27026
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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