HCID 58635223, compound → HCID 58635224, compound

HRID 1826606Notes

Reaction equation

HRID 1826606 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[NH:10][C@H:11]1[CH2:15][C:14](=[O:16])[O:13][C@@H:12]1[O:17][CH2:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[CH2:1]([O:8][C:9](=[O:20])[NH:10][C@H:11]1[CH2:15][C:14](=[O:16])[O:13][C@H:12]1[O:17][CH2:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58635223HCID 58635223, compound

Product 1

HCID 58635224HCID 58635224, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (2S,3S) (2-Ethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester (0.43 g, 1.54 mmol) in Ethyl acetate (50 mL) at room temperature was added 10 mol % Pd/C (˜0.05 g). The reaction flask was purged between H2 (1 atm) and vacuum three times before stirring under H2 (1 atm) at room temperature. After stirring at room temperature for 3 hrs, the reaction mixture was filtered through celite and then evaporated to dryness to give the title compound (0.21 g, 94%) as a clear oil. 1HNMR (CDCl3) δ 5.17 (d, J=1.2 Hz, 1H), 3.93-3.82 (dq, J=9.6, 7.2 Hz, 1H), 3.67-3.57 (dq, J=9.3, 6.9 Hz, 1H), 2.95-287 (dd, J=17.7, 6.9 Hz, 1H), 2.56-2.19 (dd, J=17.4, 2.7 Hz, 1H), 1.26-1.21 (t, J=7.2 Hz, 31H). MS(ES) for C6H11NO3 (MW=145.16): positive 146 ([M+]). Part C: (4S,5R)-4-Amino-5-ethoxy-dihydro-furan-2-one

Workup

  1. customThe reaction flask was purged between H2 (1 atm) and vacuum three times
  2. stirringAfter stirring at room temperature for 3 hrs
  3. filtrationthe reaction mixture was filtered through celite
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-d54d1a2986374a7c847205f91ad32060
Source dataset
uspto-grants-2006_05
Patent number
US07053056B2

Reaction notes

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