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

HRID 1252768Notes

Reaction equation

HRID 1252768 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 charcoal, 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) δ 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-b9f3c463b8d048ed965834850e3e29b2
Source dataset
uspto-grants-1988_05
Patent number
US04745188

Reaction notes

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