N-bromobutanimide → HCID 13254995, compound

HRID 434321Notes

Reaction equation

HRID 434321 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:16][CH2:17][C@H:18]1[C@H:22]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:21][CH:20]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:19]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClC(Cl)(Cl)Cl>[C:20]([O:19][C@H:18]([C@H:22]([Br:1])[CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:17][O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:21])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21764986HCID 21764986, compound

Product 1

HCID 13254995HCID 13254995, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
4 °C

Procedure

10.9 g (61.2 mMol) N-bromosuccinimide are suspended in 150 ml tetrachloromethane, the suspension cooled to 4° C. and 23.9 g (61.2 mMol) of (4S,5S)-4,5-dibenzyloxymethyl-2-phenyl-1,3-dioxolan dissolved in 250 ml tetrachloromethane added dropwise at the same temperature over a period of 50 minutes. The cooling bath is removed, the reaction flask wrapped in aluminium foil and the reaction mixture stirred for 3 days at room temperature. The obtained orange coloured suspension is diluted with 1 liter methylene chloride and shaken with 200 ml saturated sodium bicarbonate solution. The aqueous phase is extracted with 300 ml methylene chloride and the combined organic phases are dried over sodium sulfate, filtered through a layer of talc and evaporated under vacuum. The residue is chromatographed using 1 kg of silica gel 60 and methylene chloride as eluant. The title compound is obtained as a colourless oil: rotation, [α]D22 =+18.7°, (c=1.3 in chloroform).

Workup

  1. additionadded dropwise at the same temperature over a period of 50 minutes
  2. customThe cooling bath is removed
  3. additionis diluted with 1 liter methylene chloride
  4. stirringshaken with 200 ml saturated sodium bicarbonate solution
  5. extractionThe aqueous phase is extracted with 300 ml methylene chloride
  6. dry with materialthe combined organic phases are dried over sodium sulfate
  7. filtrationfiltered through a layer of talc
  8. customevaporated under vacuum
  9. customThe residue is chromatographed

Sources & evidence

ORD record
ord-590d979b2d8649e19aa43c4f9e84d099
Source dataset
uspto-grants-1983_08
Patent number
US04396542

Reaction notes

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