Hydrochloric Acid → Rac-5-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-oxazolidin-2-one

HRID 1640529Notes

Reaction equation

HRID 1640529 reaction equation
C([O:8][C:9](=O)[NH:10][C:11]1[CH:20]=[CH:19][C:14]2[O:15][CH2:16][CH2:17][O:18][C:13]=2[CH:12]=1)C1C=CC=CC=1.[C:22]([Si:26]([CH3:36])([CH3:35])[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]1[CH2:34][O:33]1)([CH3:25])([CH3:24])[CH3:23].C(O[Li])(C)(C)C.C1COCC1.Cl>CN(C=O)C>[C:22]([Si:26]([CH3:35])([CH3:36])[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]1[O:33][C:9](=[O:8])[N:10]([C:11]2[CH:20]=[CH:19][C:14]3[O:15][CH2:16][CH2:17][O:18][C:13]=3[CH:12]=2)[CH2:34]1)([CH3:23])([CH3:24])[CH3:25]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 13570755Rac-tert-butyl-dimethyl-(4-oxiranyl-butoxy)-silaneHCID 66736198(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-carbamic acid benzyl esterHCID 178506942HCID 178506942, compound

Product 1

HCID 66737368Rac-5-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-oxazolidin-2-oneYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2,3-dihydro-benzo[1,4]dioxin-6-yl)-carbamic acid benzyl ester (0.75 g, 2.6 mmol) and rac-tert-butyl-dimethyl-(4-oxiranyl-butoxy)-silane (prepared according to Angew. Chem. (2007), 46, 5896; 0.91 g, 1.5 eq.) in DMF (8 mL) at 0° C. was treated with a 2.2M solution of t-BuOLi in THF (3.6 mL, 3 eq.). The mixture was stirred at rt for 22 h. HCl 1M (5.3 mL) was added and the mixture partitioned between EA and water. The org. phase was washed with water and brine, dried over MgSO4 and concentrated. The product was purified by FC (Hex/EA 1:1, 1:2) to give the title intermediate as a yellowish oil (0.87 g, 81% yield).

Workup

  1. customthe mixture partitioned between EA and water
  2. washphase was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe product was purified by FC (Hex/EA 1:1, 1:2)

Sources & evidence

ORD record
ord-d3852a30700c46a3a26e2e4a7ca013b5
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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