Sodium Hydroxide → HCID 56616151, compound

HRID 375719Notes

Reaction equation

HRID 375719 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([O:36][C:37](=[O:39])[CH3:38])[C:8]2[CH2:19][S:18][CH2:17][C@@H:16]([C:20]([O:22][CH3:23])=[O:21])[NH:15][C:14](=[O:24])[C@@H:13]([NH:25]C(OC(C)(C)C)=O)[CH2:12][O:11][C:10](=[O:33])[C:9]=2[C:34]=1[CH3:35])(=[O:3])[CH3:2].P([O-])(O)(O)=O.[Na+].[OH-].[Na+]>FC(F)(F)C(O)=O>[C:1]([O:4][C:5]1[CH:6]=[C:7]([O:36][C:37](=[O:39])[CH3:38])[C:8]2[CH2:19][S:18][CH2:17][C@@H:16]([C:20]([O:22][CH3:23])=[O:21])[NH:15][C:14](=[O:24])[C@@H:13]([NH2:25])[CH2:12][O:11][C:10](=[O:33])[C:9]=2[C:34]=1[CH3:35])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 23672064Monosodium phosphateHCID 54045675HCID 54045675, compound

Product 1

HCID 56616151HCID 56616151, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 114 mg of t-butyl (4R,75)-12,14-diacetoxy-1,3,4,5,6,7,8,10-octahydro-4-methoxycarbonyl-11-methyl-6,10-dioxo -9,2,5-benzoxathiaazacyclododecine-7-carbamate in 2.4 ml of trifiuoroacetic acid was stirred at 0° C. for 30 minutes. The solution was poured onto a mixture of 20 ml of 0.5M aqueous sodium dihydrogenphosphate solution, 4.7 ml of 28% aqueous sodium hydroxide solution and crushed ice. The pH was adjusted to 9 by the addition of sodium hydroxide and the mixture was then extracted with methylene chloride. The organic layer was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was dissolved in methylene chloride and crystallized by the addition of n-hexane to give methyl (4R,7S)-12,14-diacetoxy-7-amino-1,3,4,5,6,7,8,10-octahydro-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-4-carboxylate as a white powder.

Workup

  1. customcrushed ice
  2. extractionthe mixture was then extracted with methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in methylene chloride
  7. customcrystallized by the addition of n-hexane

Sources & evidence

ORD record
ord-38c18cfc4db44ee48846a0e676749152
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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