Tetra-n-butylammonium tribromide → HCID 86727349, compound

HRID 518994Notes

Reaction equation

HRID 518994 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][CH:26]=2)[O:23][CH2:22][C:21]2[N:16]3[CH:17]([CH3:28])[C:18](=[O:27])[NH:19][N:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br-:29].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[Br:29])[O:23][CH2:22][C:21]2[N:16]3[CH:17]([CH3:28])[C:18](=[O:27])[NH:19][N:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 86727348HCID 86727348, compound

Product 1

HCID 86727349HCID 86727349, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester (0.234 g, 0.603 mmol) in DCM (4 mL) and MeOH (2 mL) was added tetrabutylammonium tribromide (0.291 g, 0.603 mmol) and the mixture was stirred at ambient temperature for 2 h. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (eluting with 30% EtOAc in petroleum ether) to give 3-(7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester (0.267 g, 95%). LC/MS (Table 1, Method 2) Rt=1.217 min.; MS m/z: 467/469 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography on silica gel (eluting with 30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-34c2bec6ba4446e086cc6243a413035a
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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