HCID 68653695, compound → HCID 68653245, compound

HRID 499699Notes

Reaction equation

HRID 499699 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]([C:17]([O:19]CC2C=CC=CC=2)=[O:18])([CH3:16])[CH3:15])[CH2:11][O:10][C:9]1([CH3:28])[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]([C:17]([OH:19])=[O:18])([CH3:16])[CH3:15])[CH2:11][O:10][C:9]1([CH3:28])[CH3:27])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68653695HCID 68653695, compound

Product 1

HCID 68653245HCID 68653245, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9.48 g of 4(S)-(2-benzyloxycarbonyl-2-methyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester and 2.58 g of 10% Pd/C in 100 ml of ethyl acetate is hydrogenated at room temperature for 4.5 hours. The solid is removed by filtration over Hyflo®. The mixture is concentrated and re-dissolved in ethyl acetate and 2N NaOH. The layers are separated and the aqueous layer is extracted with ethyl acetate (2×). The aqueous layer is acidified to pH 3 with 4M HCl and extracted with ethyl acetate (3×). The combined organic layers from the second extraction are dried over sodium sulphate, filtered and concentrated. The crude title compound is obtained as a colourless oil. Rf=0.43 (EtOAc-heptane 1:1); Rt=4.23 (gradient I).

Workup

  1. customThe solid is removed by filtration over Hyflo®
  2. concentrationThe mixture is concentrated
  3. dissolutionre-dissolved in ethyl acetate
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with ethyl acetate (2×)
  6. extractionextracted with ethyl acetate (3×)
  7. extractionThe combined organic layers from the second extraction
  8. dry with materialare dried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-cd8d40a739064b009d8afde675996fc0
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

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