HCID 86760513, compound → HCID 86760512, compound

HRID 1295482Notes

Reaction equation

HRID 1295482 reaction equation
C(OC([NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C@H:21]([O:27][CH2:28][CH3:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=1)=O)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[NH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C@H:21]([O:27][CH2:28][CH3:29])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 86760513HCID 86760513, compound

Product 1

HCID 86760512HCID 86760512, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl (2S)-3-[4-(2-{[(benzyloxy)carbonyl]amino}ethyl)phenyl]-2-ethoxypropanoate (2.45 g, 6.14 mmol) was hydrogenated for 2.5 hours at atmospheric pressure in ethyl acetate (51 ml) using Pd/C (1 spoon) as catalyst. After filtration on hyflo, the solvent was evaporated in vacuo. The crude product was purified by chromatography on silica gel using THF:methanol (NH3-saturated) (gradient 25:1–1:25) as eluent. The first fractions containing the product was filtered on Millipore filter and combined with the later fractions containing product to give 0.84 g (yield 52%, including a by-product) of the desired product.

Workup

  1. filtrationAfter filtration on hyflo
  2. customthe solvent was evaporated in vacuo
  3. customThe crude product was purified by chromatography on silica gel
  4. additionThe first fractions containing the product
  5. filtrationwas filtered on Millipore
  6. filtrationfilter
  7. additioncontaining product
  8. customto give 0.84 g (yield 52%

Sources & evidence

ORD record
ord-8c80c8bb36954e7e9d74dd42692eca39
Source dataset
uspto-grants-2007_07
Patent number
US07241923B2

Reaction notes

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