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

HRID 2295323Notes

Reaction equation

HRID 2295323 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 (Me2 CO-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, CH2 CO2), 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-aca135f314b64bd5842bbd84982d156b
Source dataset
uspto-grants-1984_01
Patent number
US04424230

Reaction notes

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