tert-Butyl piperazine-1-carboxylate → HCID 117875526, compound

HRID 1525123Notes

Reaction equation

HRID 1525123 reaction equation
I[CH2:2][C@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:10]=[CH:11][C:12]3[S:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=3[CH:19]=2)[CH2:4]1.[C:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CN(C=O)C.O.CC(OC)(C)C>[C:23]([O:22][C:20]([N:27]1[CH2:32][CH2:31][N:30]([CH2:2][C@H:3]2[O:7][C:6](=[O:8])[N:5]([C:9]3[CH:10]=[CH:11][C:12]4[S:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=4[CH:19]=3)[CH2:4]2)[CH2:29][CH2:28]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 66751595HCID 66751595, compound

Product 1

HCID 117875526HCID 117875526, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 6-((S)-5-iodomethyl-2-oxooxazolidin-3-yl)-4H-benzo[1,4]thiazin-3-one (prepared according to WO 2008/126034; 1.0 g) and Boc-piperazine (1.43 g) in DMF (10 ml) was stirred overnight at rt and 2 h at 60° C. The reaction mixture was allowed to reach rt, diluted with water and extracted with EA (2×). The combined org. layers were washed with water and brine, dried over MgSO4, filtered and evaporated under reduced pressure, affording after stirring the residue in TBME a colourless solid.

Workup

  1. customto reach rt
  2. extractionextracted with EA (2×)
  3. washlayers were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customaffording

Sources & evidence

ORD record
ord-f28749d4839c49df90ed6333a84d5c43
Source dataset
uspto-grants-2015_07
Patent number
US09079922B2

Reaction notes

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