tert-butyl N-(2-hydroxyethyl)carbamate → HCID 68856042, compound

HRID 494930Notes

Reaction equation

HRID 494930 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:19]([O:23][C:24]([NH:26][CH2:27][CH2:28]O)=[O:25])([CH3:22])([CH3:21])[CH3:20].CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[C:19]([O:23][C:24]([NH:26][CH2:27][CH2:28][O:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 5363146Diisopropyl azodicarboxylateHCID 57682806HCID 57682806, compound

Product 1

HCID 68856042HCID 68856042, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.00 g of methyl 2-hydroxy-4-methoxy-5-(3-methyl-2-butenyl)benzoate, 1.29 g of N-(t-butoxycarbonyl)-2-aminoethanol, and 2.31 g of triphephenylphosphine were dissolved in 50 ml of tetrahydrofuran. The obtained mixture was cooled on ice. Thereafter, 1.73 ml of diisopropylazodicarboxylate was added to the reaction solution at the same temperature, and the temperature was then raised to a room temperature. After completion of the reaction, the reaction solution was concentrated. The residue was purified by NH silica gel column chromatography (hexane/ethyl acetate), so as to obtain 1.54 g of methyl 2-(2-t-butoxycarbonylaminoethoxy)-4-methoxy-5-(3-methyl-2-butenyl)benzoate. The obtained product was dissolved in 15 ml of methanol, and the obtained mixture was cooled on ice. Thereafter, 10 ml of a 4 N hydrochloric acid-ethyl acetate solution was added to the reaction solution. After completion of the reaction, the reaction solution was concentrated under a reduced pressure. Ethyl acetate was added to the residue, and the obtained mixture was adjusted to be approximately pH 11 with addition of a 5 N sodium hydroxide aqueous solution and a saturated sodium bicarbonate aqueous solution. The organic layer was dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. 1.06 g of the obtained residue was dissolved in 20 ml of toluene, and the obtained solution was heated to reflux. After completion of the reaction, the reaction solution was concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 601 mg of the subject compound.

Workup

  1. temperatureThe obtained mixture was cooled on ice
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated
  4. customThe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b5fa7d4608564c26ad3a9e0a9ad1bff8
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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