Bromine → HCID 18451947, compound

HRID 1725612Notes

Reaction equation

HRID 1725612 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH:9]1([CH2:12][N:13]2[C:19](=[O:20])[CH2:18][CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:14]2)[CH2:11][CH2:10]1.[Br:34]Br>O1CCCC1>[Br:34][CH:18]1[CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[CH:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:14][N:13]([CH2:12][CH:9]2[CH2:10][CH2:11]2)[C:19]1=[O:20]

Participants

5

Reactant 3

HCID 24408BromineHCID 2724682Lithium diisopropylamideHCID 18451945HCID 18451945, compound

Product 1

HCID 18451947HCID 18451947, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium diisopropylamide (1 M in THF; 2.13 mL, 2.13 mmol) was added to tert-butyl 4-(cyclopropylmethyl)-5-oxo-2-phenyl-1,4-diazepane-1-carboxylate (0.489 g, 1.42 mmol) in tetrahydrofuran (5 mL) at −78° C. After 30 min, the enolate solution was transferred dropwise via cannula to a solution of bromine (0.36 mL, 7.10 mmol) in tetrahydrofuran (3 mL) at −78° C. over a period of 5 min. After 15 min, the mixture was quenched with aqueous saturated sodium sulfite and allowed to warm to ambient temperature. The mixture was extracted with ethyl acetate, washed with saturated 50 aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate, filtered, and concentrated. MS 423 (M+1).

Workup

  1. waitAfter 15 min
  2. customthe mixture was quenched with aqueous saturated sodium sulfite
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with saturated 50 aqueous sodium bicarbonate and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b09a4c833ebd4078a8eb2675327671e8
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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