Citric Acid → HCID 67722311, compound

HRID 2258298Notes

Reaction equation

HRID 2258298 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[C:7]([O:11][C:12]([NH:14][C@@:15]([CH2:21][C@@H:22]1[O:26][C:25]([CH3:28])([CH3:27])[NH:24][C@H:23]1[CH2:29][C@H:30]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([O:43][CH2:44][CH2:45][CH2:46][O:47][CH3:48])[CH:36]=1)[CH:31]([CH3:33])[CH3:32])([CH:18]([CH3:20])[CH3:19])[CH:16]=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].S([O-])([O-])=[O:50].[Na+].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[C:7]([O:11][C:12]([NH:14][C@@:15]([CH2:21][C@@H:22]1[O:26][C:25]([CH3:28])([CH3:27])[NH:24][C@H:23]1[CH2:29][C@H:30]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([O:43][CH2:44][CH2:45][CH2:46][O:47][CH3:48])[CH:36]=1)[CH:31]([CH3:32])[CH3:33])([CH:18]([CH3:19])[CH3:20])[C:16]([OH:50])=[O:17])=[O:13])([CH3:8])([CH3:9])[CH3:10]

Participants

8

Reactant 4

HCID 311Citric AcidHCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 86751174HCID 86751174, compound

Product 1

HCID 67722311HCID 67722311, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

Water (470 ml), potassium permanganate (79.1 g) and tetrabutylammonium bromide (9.7 g) are added in succession at 0° C., with stirring, to a solution of N-(tert-butoxycarbonyl)amino-2(S)-{4(S)-[2(S)-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-3-methyl-butyl]-2,2-dimethyloxazolidin-5(S)-ylmethyl}-3-methyl-butyraldehyde (53.0 g) in toluene (470 ml). The reaction mixture is stirred for 48 hours at 0°-5° C. and then, at 10% sodium sulfite solution (1.2 liters) and, after a further 30 minutes, 10% citric acid solution (1.95 liters) and water (1.2 liters) are added. The mixture is extracted with ethyl acetate (3×2.5 liters), and the organic phases are washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated. Purification of the crude product by FC (2.3 kg of silica gel, ethyl acetate/hexane 3:7) yields the pure title compound in the form of an oil (31.7 g): Rf (ethyl acetate/hexane 1:2)=0.21; Anal. C33H55NO8 (593.80): calc. C, 66.75; H, 9.34; N, 2.36; found C, 66.69; H, 9.39; N, 2.39.

Workup

  1. extractionThe mixture is extracted with ethyl acetate (3×2.5 liters)
  2. washthe organic phases are washed with water and saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification of the crude product by FC (2.3 kg of silica gel, ethyl acetate/hexane 3:7)

Sources & evidence

ORD record
ord-97fa2bba5d3a4b91805233c8b5095a88
Source dataset
uspto-grants-1997_08
Patent number
US05659065

Reaction notes

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