1,4-Dioxane → HCID 86670841, compound

HRID 709369Notes

Reaction equation

HRID 709369 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][NH:10][C:11]([CH:13]2[CH2:17][C:16]3([CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH2:15][N:14]2[C:23](=[O:33])[C@@H:24]([NH:28][C:29](=[O:32])[O:30][CH3:31])[CH:25]([CH3:27])[CH3:26])=O)=[CH:4][CH:3]=1.O1CCOCC1.C([O-])(=O)C.[NH4+:45]>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:45][C:11]([CH:13]3[CH2:17][C:16]4([CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH2:15][N:14]3[C:23](=[O:33])[C@@H:24]([NH:28][C:29](=[O:32])[O:30][CH3:31])[CH:25]([CH3:27])[CH3:26])=[N:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 517165Ammonium AcetateHCID 86670840HCID 86670840, compound

Product 1

HCID 86670841HCID 86670841, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

In a 10 ml seal tube, methyl (2S)-1-(3-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-8-oxa-2-azaspiro[4.5]decan-2-yl)-3-methyl-1-oxobutan-2-ylcarbamate (200 mg, 371 μmol) was combined with dioxane (6 ml) to give a colorless solution. Ammonium acetate (286 mg, 3.71 mmol) was added and it was stirred at 110° C. overnight. It was cooled and diluted with EtOAc (10 ml). The mixture was filtered and concentrated in vacuo to afford methyl (2S)-1-(3-(5-(4-bromophenyl)-1H-imidazol-2-yl)-8-oxa-2-azaspiro[4.5]decan-2-yl)-3-methyl-1-oxobutan-2-ylcarbamate as a yellow solid (170 mg, 88.1%). ESI-LRMS m/e calcd for C24H31BrN4O4 [M+] 519. found 520 [M+H+].

Workup

  1. customIn a 10 ml seal tube
  2. customto give a colorless solution
  3. temperatureIt was cooled
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-412a745042b3484793c572c9f376cfd8
Source dataset
uspto-grants-2015_11
Patent number
US09180193B2

Reaction notes

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