Triphenylphosphine → HCID 71681343, compound

HRID 929897Notes

Reaction equation

HRID 929897 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[C:22]([O:26][C:27]([C@:29]1([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:34][C@H:33](O)[C@@H:32]2[C@H:30]1[C@H:31]2[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:28])([CH3:25])([CH3:24])[CH3:23]>C1(C)C=CC=CC=1.N1C=CC=CC=1.C(OCC)(=O)C>[C:22]([O:26][C:27]([C@:29]1([NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:34][C@@H:33]([Br:20])[C@@H:32]2[C@H:30]1[C@H:31]2[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 59712892ditert-butyl(1S,2S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate

Product 1

HCID 71681343HCID 71681343, compoundYield 78.2%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Dissolve triphenylphosphine (41.97 g, 158.4 mmol) in fresh toluene (660 mL) and add bromine (8.14 mL, 158.4 mmol) until a yellow color persists. Add dropwise a solution of ditert-butyl(1S,2S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate (32.75 g, 79.2 mmol) in toluene (176 mL) and anhydrous pyridine (528 mL) during 45 min. Stir the reaction at 75° C. overnight. Cool to room temperature, dilute with ethyl acetate, filter and concentrate to dryness. Slurry the crude in methyl tert-butyl ether, filter to remove the solids and concentrate the filtrate to dryness. Purify the crude by silica gel chromatography (750 g) eluting with hexane:ethyl acetate (0:100 to 80:20) to obtain the title compound as a white solid (29.52 g, 78%). MS (m/z): 498, 500 (M+23).

Workup

  1. customthe reaction at 75° C. overnight
  2. filtrationfilter
  3. concentrationconcentrate to dryness
  4. filtrationfilter
  5. customto remove the solids
  6. concentrationconcentrate the filtrate to dryness
  7. customPurify the crude by silica gel chromatography (750 g)
  8. washeluting with hexane:ethyl acetate (0:100 to 80:20)

Sources & evidence

ORD record
ord-b158deb98977420782a46409727c1b87
Source dataset
uspto-grants-2016_03
Patent number
US09296710B2

Reaction notes

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