N-(t-butyldimethylsilyl)-4-(3-benzyloxycarbonyl-2-hydroxypropyl)-azetidin-2-one → N-(t-butyldimethylsilyl)-4-(3-carboxy-2-hydroxypropyl)-azetidin-2-one

HRID 1493484Notes

Reaction equation

HRID 1493484 reaction equation
[Si:1]([N:8]1[CH:11]([CH2:12][CH:13]([OH:25])[CH2:14][C:15]([O:17]CC2C=CC=CC=2)=[O:16])[CH2:10][C:9]1=[O:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>[Pd].C(O)C>[Si:1]([N:8]1[CH:11]([CH2:12][CH:13]([OH:25])[CH2:14][C:15]([OH:17])=[O:16])[CH2:10][C:9]1=[O:26])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 12804719N-(t-butyldimethylsilyl)-4-(3-benzyloxycarbonyl-2-hydroxypropyl)-azetidin-2-one

Product 1

HCID 15136308N-(t-butyldimethylsilyl)-4-(3-carboxy-2-hydroxypropyl)-azetidin-2-oneYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of crude N-(t-butyldimethylsilyl)-4-(3-benzyloxycarbonyl-2-Hydroxypropyl)-azetidin-2-one (13.46 g, 35.6 mmol), 10% palladium on charcoa, and ethanol (200 ml) is hydrogenated at 40 psi for 30 mins. The mixture is filtered and the filtrate is evaporated under vacuum and stripped with toluene to give N-(t-butyldimethylsilyl)-4-(3-carboxy-2-hydroxypropyl)-azetidin-2-one (9.51 g) as an off-white solid: IR (neat film from Me2CO) 3200 (br), 1735, and 1700 (shifts to 1590 with Et3N) cm-1 ; NMR (Me2CO-d6) 8 0.25 (s,6,2CH3), 0.98 (s,9,C(CH3)3) 1.17-2.33 (m,2,CH--C CH2 --CH), 2.50 (d,2,J=6.5, CH2CO2), 2.50-3.40 (m,2,H3 and H3β), 3.97 (m,2,H4 and CHOH); MS on bistrimethylsilyl derivative m/e 431 (M+), 416 (M+-57) and 332 (374-42).

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated under vacuum

Sources & evidence

ORD record
ord-05707bb103544f6bb8b0f15e5e52baf0
Source dataset
uspto-grants-1991_06
Patent number
US05021566

Reaction notes

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