Tetrahydrofuran → tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamate

HRID 1024548Notes

Reaction equation

HRID 1024548 reaction equation
C(O[CH2:5][C@@H:6]([O:23]S(C)(=O)=O)[C@@H:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.C1COCC1.C([O-])([O-])=O.[K+].[K+]>CO>[O:23]1[CH2:5][C@H:6]1[C@@H:7]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 11475108(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-[(methylsulfonyl)oxy]-4-phenylbutyl acetate

Product 1

HCID 9813904tert-Butyl {(1S)-1-[(2R)-oxiran-2-yl]-2-phenylethyl}carbamateYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a suitable reactor was added 5 (2 g, 4.98 mmol), THF (20 mL), MeOH (20 mL), and K2CO3 (1.5 g, 10.96 mmol) at 20-30° C. under N2. The mixture was stirred at 20-30° C. for 15 hr. The mixture was filtered, and the filtrate was concentrated at 40-50° C. under reduced pressure to yield a pale yellow oil. After being purified by flash column chromatography, 6 was obtained as a white solid in 90% yield.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated at 40-50° C. under reduced pressure
  3. customto yield a pale yellow oil
  4. customAfter being purified by flash column chromatography
  5. custom6 was obtained as a white solid in 90% yield

Sources & evidence

ORD record
ord-86b9cc1eedc54bbeb7bff51a2bf76770
Source dataset
uspto-grants-2014_05
Patent number
US08722921B2

Reaction notes

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