Tetrapropylammonium → 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

HRID 725637Notes

Reaction equation

HRID 725637 reaction equation
C[N+]1([O-])CCOCC1.[C:9]([O:13][C:14]([N:16]1[C@@H:20]([CH2:21][C@@H:22]([CH:38]([CH3:40])[CH3:39])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[CH:25]=2)[C@H:19]([CH2:41][C@@H:42]([CH:45]([CH3:47])[CH3:46])[CH2:43][OH:44])[O:18][C:17]1([CH3:49])[CH3:48])=[O:15])([CH3:12])([CH3:11])[CH3:10].C([N+](CCC)(CCC)CCC)CC>ClCCl>[C:9]([O:13][C:14]([N:16]1[C@@H:20]([CH2:21][C@@H:22]([CH:38]([CH3:40])[CH3:39])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[CH:25]=2)[C@H:19]([CH2:41][C@H:42]([CH:43]=[O:44])[CH:45]([CH3:46])[CH3:47])[O:18][C:17]1([CH3:48])[CH3:49])=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 236253313-Oxazolidinecarboxylic acid, 5-[(2S)-2-(hydroxymethyl)-3-methylbutyl]-4-[(2S)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4S,5S)-

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 g of molecular sieve (0.3 nm) and 16.6 g of N-methylmorpholine-N-oxide are added to 53 g of 3-tert-butoxycarbonyl-5(S)-(3-hydroxy-2(S)-isopropyl-propyl)-4(S)-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine in 1.8 liters of dichloromethane at room temperature. The reaction mixture is stirred for 10 minutes and then 1.60 g of tetrapropylammonium perrutherate are added. The reaction mixture is stirred for a further 30 minutes and then filtered. The filtrate is diluted with dichloromethane and then washed in succession with 2M sodium sulfite solution, saturated sodium chloride solution and 1M copper(II) sulfate. The organic phase is concentrated by evaporation and the crude title compound is obtained: Rf (ethyl acetate/hexane=1:2)=0.43.

Workup

  1. stirringThe reaction mixture is stirred for a further 30 minutes
  2. filtrationfiltered
  3. additionThe filtrate is diluted with dichloromethane
  4. washwashed in succession with 2M sodium sulfite solution, saturated sodium chloride solution and 1M copper(II) sulfate
  5. concentrationThe organic phase is concentrated by evaporation

Sources & evidence

ORD record
ord-b09e860cf3304b039e5b526b411e3a85
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

Loading…