2,2-Dimethoxypropane → 4-[N-Tert-butoxycarbonyl-2,2-dimethyl-4(S)-(2,2-dimethyl-4-triisopropylsilyloxybutyl)-1,3-oxazolidin-5(S)-yl]-but-1-ene

HRID 863232Notes

Reaction equation

HRID 863232 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:16][C:17]([CH3:32])([CH3:31])[CH2:18][CH2:19][O:20][Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[C@@H:10]([OH:15])[CH2:11][CH2:12][CH:13]=[CH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[C:35](OC)([CH3:37])[CH3:36].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@@H:9]([CH2:16][C:17]([CH3:31])([CH3:32])[CH2:18][CH2:19][O:20][Si:21]([CH:25]([CH3:26])[CH3:27])([CH:22]([CH3:23])[CH3:24])[CH:28]([CH3:30])[CH3:29])[C@H:10]([CH2:11][CH2:12][CH:13]=[CH2:14])[O:15][C:35]1([CH3:37])[CH3:36])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 228825826(S)-Tert-butoxycarbonylamino-8,8-dimethyl-5(S)-hydroxy-10-triisopropylsilyloxydec-1-ene

Product 1

HCID 228824874-[N-Tert-butoxycarbonyl-2,2-dimethyl-4(S)-(2,2-dimethyl-4-triisopropylsilyloxybutyl)-1,3-oxazolidin-5(S)-yl]-but-1-ene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.80 g of 6(S)-tert-butoxycarbonylamino-8,8-dimethyl-5(S)-hydroxy-10-triisopropylsilyloxydec1-ene are stirred in 10 ml each of methylene chloride and dimethoxypropane with 50 mg of p-toluenesulfonic acid hydrate at room temperature for 2 h. After the mixture has been concentrated, the residue is purified over 250 g of silica gel with a 1:20 mixture of ethyl acetate and hexane as the mobile phase: Rf (1:20 mixture of ethyl acetate and hexane)=0.40.

Workup

  1. concentrationAfter the mixture has been concentrated
  2. customthe residue is purified over 250 g of silica gel with a 1:20 mixture of ethyl acetate and hexane as the mobile phase
  3. additionRf (1:20 mixture of ethyl acetate and hexane)=0.40

Sources & evidence

ORD record
ord-7a9a925a368a4531b350e9259cc3b3cb
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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