Methanol → Methyl (+/-)-(cis)-(7-bromo-8-fluoro-1,3,4,14b-tetrahydro-4-oxo-2H-dibenzo [b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamate

HRID 1668346Notes

Reaction equation

HRID 1668346 reaction equation
[Br:1][C:2]1[C:24]([F:25])=[CH:23][C:5]2[O:6][C:7]3[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=3[C@H:9]3[C@H:14](C(O)=O)[CH2:13][CH2:12][C:11](=[O:18])[N:10]3[C:4]=2[CH:3]=1.C([N:28]([CH2:31]C)CC)C.P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)[O:34][C:35]1C=CC=CC=1.C[OH:53]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:24]([F:25])=[CH:23][C:5]2[O:6][C:7]3[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=3[C@H:9]3[C@H:14]([NH:28][C:31](=[O:53])[O:34][CH3:35])[CH2:13][CH2:12][C:11](=[O:18])[N:10]3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 67358795HCID 67358795, compound

Product 1

HCID 86619611Methyl (+/-)-(cis)-(7-bromo-8-fluoro-1,3,4,14b-tetrahydro-4-oxo-2H-dibenzo [b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)carbamateYield 217%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (±)-(cis)-7-bromo-8-fluoro-1,3,4,14b-tetrahydro-4-oxo-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-carboxylic acid (13.1 g, 32.3 mmol) in toluene (660 mL), triethylamine (7.6 mL, 54 mmol) and diphenyl phosphorazidate (9.1 mL, 42 mmol) were added. The reaction mixture was heated to reflux for 2 h. Subsequently, methanol (31.9 mL, 787 mmol) was added and stirring was continued for 2 h at 70 ° C. After cooling down to room temperature, the reaction mixture was dried over P.S. filter and evaporated, to give the crude title compound (30.5 g, 100%) which was used without further purification. (m/z)=435+437 (M+H)−.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. customthe reaction mixture was dried over P.S
  4. filtrationfilter
  5. customevaporated

Sources & evidence

ORD record
ord-cc6a58857ae34808b2fe3f40276ddaac
Source dataset
uspto-grants-2011_08
Patent number
US07989442B2

Reaction notes

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