HCID 13895036, compound → HCID 3292430, compound

HRID 654062Notes

Reaction equation

HRID 654062 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-]>[Pd].C(O)C.O>[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

5

Reactant 1

HCID 13895036HCID 13895036, compound

Product 1

HCID 3292430HCID 3292430, compoundYield 6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The fast moving diastereoisomer of benzyl 5-azido-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate (0.76 g, 23.9 mmol) was hydrogenated over 5% palladium on carbon catalyst in ethanol (20 ml) and water (5 ml) for one hour. The catalyst was filtered off and the filtrate evaporated. The residual gum was triturated with ether to yield, after filtration the title compound as a pale yellow solid (456 mg, 97%). The yellow coloured impurity was removed by trituration with ethyl acetate. The title compound (400 mg) was further purified by column chromatography on silica gel (Merck Art. 9385) using water/ethanol (15:85) as eluant to yield the title compound (290 mg) as a white solid containing 1/7 molar equivalent of ethanol. δH (D2O, 400 MHz) 1.16 (t, CH3CH2OH), 1.84 (2H, m), 3.00 (2H, t, J 3.9 Hz), 3.15 (2H, m), 3.50 (1H, m), 3.58 (1H, m), 3.63 (q, CH3CH2OH), 4.07 (1H, d, J 5.4 Hz), 4.19 (1H, m), δC (D2O, 100 HMz), 31.66, 36.12, 37.61, 40.99, 63.19, 69.54, 174.79, and 174.97. Recrystallisation of a sample from aqueous methanol gave white prisms m.p. 130°-135°. νmax (KBr) 3349, 1723, 1653, 1611, 1390, 918 and 769. (Found: C, 43.93; H, 7.40; N, 12.49%. C8H14N2O4.H2O requires C, 43.63; H, 7.32; N, 12.72)

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. customThe residual gum was triturated with ether
  4. customto yield
  5. filtrationafter filtration the title compound as a pale yellow solid (456 mg, 97%)
  6. customThe yellow coloured impurity was removed by trituration with ethyl acetate
  7. customThe title compound (400 mg) was further purified by column chromatography on silica gel (Merck Art. 9385)

Sources & evidence

ORD record
ord-5a3eabb5a00d41d497cc62dadf25da56
Source dataset
uspto-grants-1992_07
Patent number
US05130241

Reaction notes

Loading…