Water → HCID 3292430, compound

HRID 654061Notes

Reaction equation

HRID 654061 reaction equation
[N:1]([CH2:4][CH2:5][CH:6]([OH:23])[CH:7]([N:18]1[CH2:21][CH2:20][C:19]1=[O:22])[C:8]([O:10]CC1C=CC=CC=1)=[O:9])=[N+]=[N-].O.CCOCC>C(O)C.[Pd]>[NH2:1][CH2:4][CH2:5][CH:6]([OH:23])[CH:7]([N:18]1[CH2:21][CH2:20][C:19]1=[O:22])[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 13895036HCID 13895036, compound

Product 1

HCID 3292430HCID 3292430, compoundYield 29.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 5-azido-3-hydroxy-2-(2-oxo-azetidin-1-yl)valerate (1.6 g, 5 mmol) as a mixture of diastereoisomers prepared as Example 1, was hydrogenated at atmospheric pressure in ethanol (45 ml) and water (7 ml) with 5% palladium on carbon catalyst (900 mg). When no more hydrogen was absorbed the reaction mixture was filtered and the filtrate evaporated to yield a gum. Trituration with ether yielded a solid which was filtered off and dried under vacuum to yield a friable foam. The foam was triturated with methanol to give a white solid and pale yellow solution. The solid was filtered off and dried to yield the less soluble diasteroisomer of the title compound (294 mg) as a white powder m.p. 152°-153.5°. νmax (KBr) 3422, 1709, 1637, 1578, 1376, 1333, 1248, 1228 and 1151; δH (D2O, 250 MHz) 1.93 (2H, m), 3.03 (2H, t, J 4 Hz), 3.21 (2H, m), 3.55 (2H, m), and 4.21 (2H, m); δC (D2O, 100 MHz) 31.06, 36.23, 37.99, 41.03, 62.49, 69.54, 172.40 and 174.74. (Found: C, 45.85, H, 6.77; N, 12.94%; C8H14N2O4 1/2H2O requires C, 45.49; H, 7.16; N, 13.26%).

Workup

  1. customWhen no more hydrogen was absorbed the reaction mixture
  2. filtrationwas filtered
  3. customthe filtrate evaporated
  4. customto yield a gum
  5. filtrationwas filtered off
  6. customdried under vacuum
  7. customto yield a friable foam
  8. customThe foam was triturated with methanol
  9. customto give a white solid and pale yellow solution
  10. filtrationThe solid was filtered off
  11. customdried

Sources & evidence

ORD record
ord-ff18d7972a4f4281be73d2d54ca6a4bb
Source dataset
uspto-grants-1992_07
Patent number
US05130241

Reaction notes

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