HCID 69055921, compound → HCID 69062874, compound

HRID 1727223Notes

Reaction equation

HRID 1727223 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]2[O:13][N:14]([CH3:22])[C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[C@:11]2([O:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:10][C@H:9]1[C:31]([OH:33])=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[Cl:21][C:20]1[C:15]2[N:14]([CH3:22])[O:13][CH:12]3[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([C:31]([OH:33])=[O:32])[CH2:10][C@@:11]3([O:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:16]=2[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 69055921HCID 69055921, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69062874HCID 69062874, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2S,3aR,9bR)-3-(tert-butoxycarbonyl)-9b-[(tert-butoxycarbonyl)oxy]-6-chloro-5-methyl-1,2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylic acid (Preparation 150, 25.4 g) in ethyl acetate (200 ml) was treated with 10% palladium on charcoal (5 g) and stirred under 50 p.s.i. of hydrogen gas for 170 hours. The reaction mixture was filtered through celite, evaporated and purified by flash column chromatography eluting with ethyl acetate:hexane (1:4) to give the product as a white foam (17.5 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customevaporated
  3. custompurified by flash column chromatography
  4. washeluting with ethyl acetate:hexane (1:4)

Sources & evidence

ORD record
ord-55531c254d7e48b5879add63d5712613
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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