2,2-Dimethoxypropane → 4-[N-Tert-butoxycarbonyl-2,2-dimethyl-4(S)-(4-triisopropylsilyloxy-2,2-dimethylbutyl)-1,3-oxazolidin-5(S)-yl]-3(R,S)-isopropylbut-1-ene

HRID 863235Notes

Reaction equation

HRID 863235 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:19][C:20]([CH3:35])([CH3:34])[CH2:21][CH2:22][O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])[C@@H:10]([OH:18])[CH2:11][CH:12]([CH:15]([CH3:17])[CH3:16])[CH:13]=[CH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[C:37]1(C)[CH:42]=CC(S(O)(=O)=O)=C[CH:38]=1.COC(OC)(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@@H:9]([CH2:19][C:20]([CH3:34])([CH3:35])[CH2:21][CH2:22][O:23][Si:24]([CH:25]([CH3:26])[CH3:27])([CH:28]([CH3:30])[CH3:29])[CH:31]([CH3:33])[CH3:32])[C@H:10]([CH2:11][CH:12]([CH:15]([CH3:17])[CH3:16])[CH:13]=[CH2:14])[O:18][C:37]1([CH3:42])[CH3:38])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 228825816(S)-Tert-butoxycarbonylamino-5(S)-hydroxy-3(R,S)-isopropyl-10-triisopropylsilyloxy-8,8-dimethyldec-1-ene

Product 1

HCID 1317205124-[N-Tert-butoxycarbonyl-2,2-dimethyl-4(S)-(4-triisopropylsilyloxy-2,2-dimethylbutyl)-1,3-oxazolidin-5(S)-yl]-3(R,S)-isopropylbut-1-ene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.4 g of 6(S)-tert-butoxycarbonylamino-8,8-dimethyl-5(S)-hydroxy-3(R,S)-isopropyl-10-triisopropylsilyloxydec-1-ene and 134 mg of p-toluenesulfonic acid hydrate are stirred in 25 ml of methylene chloride and dimethoxypropane at room temperature for 2 h. After the reaction mixture has been concentrated, the residue is purified over 500 g of silica gel by means of FC (mobile phase D): Rf (D)=0.61.

Workup

  1. concentrationAfter the reaction mixture has been concentrated
  2. customthe residue is purified over 500 g of silica gel by means of FC (mobile phase D)

Sources & evidence

ORD record
ord-eb4bbf64872147c6b1284cdbcd8d3cc3
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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