Citric Acid → 5-Oxazolidinepropanoic acid, 3-[(1,1-dimethylethoxy)carbonyl]-4-[(2S)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-2,2-dimethyl-alpha-(1-methylethyl)-, (alphaS,4S,5S)-

HRID 725636Notes

Reaction equation

HRID 725636 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C@@H:14]([CH:30]([CH3:32])[CH3:31])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:11]([CH2:33][C@H:34]([CH:38]=[O:39])[CH:35]([CH3:37])[CH3:36])[O:10][C:9]1([CH3:41])[CH3:40])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Mn]([O-])(=O)(=O)=[O:43].[K+].S([O-])([O-])=O.[Na+].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C@@H:14]([CH:30]([CH3:32])[CH3:31])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:11]([CH2:33][C@H:34]([C:38]([OH:43])=[O:39])[CH:35]([CH3:36])[CH3:37])[O:10][C:9]1([CH3:40])[CH3:41])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 311Citric AcidHCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 236253323-Tert-butoxycarbonyl-5(S)-(2(S)-formyl-3-methyl-butyl)-4(S)-(2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine

Product 1

HCID 236254795-Oxazolidinepropanoic acid, 3-[(1,1-dimethylethoxy)carbonyl]-4-[(2S)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-2,2-dimethyl-alpha-(1-methylethyl)-, (alphaS,4S,5S)-

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

53 g of 3-tert-butoxycarbonyl-5(S)-(2(S)-formyl-3-methyl-butyl)-4(S)-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine are dissolved in 470 ml of toluene, and, at 0° C., 470 ml of water, 79.1 g of potassium permanganate and 9.7 g of tetrabutylammonium bromide are added in succession thereto. The reaction mixture is stirred for a further 48 hours at 0°-5° C., and then, at 10° C., 1.2 liters of 10% sodium sulfite solution are added. After a further 30 minutes, 1.95 liters of 10% citric acid solution and 1.2 liters of water are added. The product is extracted by repeated extraction with ethyl acetate. The extracts are concentrated by evaporation and purified by FC (2.3 kg of silica gel, ethyl acetate/hexane=3:7). The title compound is obtained: Rf (ethyl acetate/hexane=1:2)=0.21.

Workup

  1. waitAfter a further 30 minutes
  2. extractionThe product is extracted
  3. extractionextraction with ethyl acetate
  4. concentrationThe extracts are concentrated by evaporation
  5. custompurified by FC (2.3 kg of silica gel, ethyl acetate/hexane=3:7)

Sources & evidence

ORD record
ord-0dbd0ffa18cc4090ba1d655d0c95f9bd
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

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