2-Methoxypropene → Methyl (S)-3-Boc-2,2-dimethyloxazolidine-4-propanoate

HRID 863214Notes

Reaction equation

HRID 863214 reaction equation
CO[C:3]([CH3:5])=[CH2:4].[C:6]([O:10][C:11]([NH:13][C@H:14]([CH2:21][OH:22])[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:12])([CH3:9])([CH3:8])[CH3:7].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[C:6]([O:10][C:11]([N:13]1[C@@H:14]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:21][O:22][C:3]1([CH3:5])[CH3:4])=[O:12])([CH3:7])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 83002-MethoxypropeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 11107667(S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate

Product 1

HCID 15930243Methyl (S)-3-Boc-2,2-dimethyloxazolidine-4-propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

120 ml of isopropenyl methyl ether are added to a solution of 159.5 g of methyl 4(S)-tert-butoxycarbonylamino-5-hydroxyvalerate and 3 g of p-toluenesulfonic acid hydrate in 500 ml of methylene chloride at 0° C. The reaction mixture is stirred at 0° C. for 2 h and at room temperature for 3 h. The reaction solution is washed with 100 ml of saturated sodium bicarbonate solution and evaporated. The title compound is obtained by FC (800 g of silica gel, mobile phase E): [α]D =+20.5 (c=0.8 in CHCl3); Rf (D)=0.24; MS: (M)+ =287.

Workup

  1. washThe reaction solution is washed with 100 ml of saturated sodium bicarbonate solution
  2. customevaporated

Sources & evidence

ORD record
ord-07f48a57eb9f4865b01ca7dfe1cda629
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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