Hydrochloric Acid → 4-[3-(p-Nitrobenzyloxycarbonyl)-2-oxopropyl]-azetidin-2-one

HRID 2198453Notes

Reaction equation

HRID 2198453 reaction equation
[Si]([N:8]1[CH:11]([CH2:12][C:13](=[O:28])[CH2:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[CH2:10][C:9]1=[O:29])(C(C)(C)C)(C)C.Cl.P([O-])([O-])(O)=O.[K+].[K+]>CO>[N+:25]([C:22]1[CH:23]=[CH:24][C:19]([CH2:18][O:17][C:15]([CH2:14][C:13](=[O:28])[CH2:12][CH:11]2[NH:8][C:9](=[O:29])[CH2:10]2)=[O:16])=[CH:20][CH:21]=1)([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24450Potassium Phosphate, DibasicHCID 12804721N-(t-butyldimethylsilyl)-4-[3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl]-azetidin-2-one

Product 1

HCID 128047224-[3-(p-Nitrobenzyloxycarbonyl)-2-oxopropyl]-azetidin-2-oneYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(t-butyldimethylsilyl)-4-[3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl]-azetidin-2-one (5.17 g, 12.3 mMol) in methanol (55 ml) is treated with 1 N hydrochloric acid (6.2 ml) and then kept at room temperature for 200 mins. The solution is treated with 1 M dipotassium hydrogenphosphate (6.2 ml) and concentrated under vacuum. The residue is taken up in ethyl acetate (100 ml), washed with brine, dried over magnesium sulfate, filtered, and evaporated under vacuum. Triturating the resulting oil with diethyl ether yields 4-[3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl]-azetidin-2-one (3.42 g, 91%) as an off-white powder: mp 50°-52°; IR (CH2Cl2) 3416, 1767, 1723, 1528, and 1352 cm-1 ; NMR (CDCl3) ε2.60 (ddd,1,J=1,2.7, and 15.1,H3β), 2.77 (dd,1,J=8.4 and 18.2, CHCH2CO), 3.13 (dd,1,J=5.1 and 18.2, CHCH2CO), 3.20 (ddd,1,J=2,4, 5.0, and 15.1, H3α), 3.57 (s,2,COCH2CO2), 3.98 (m,1,H4); 5.27 (s,2,CH2Ar), 6.28 (br,s,1,NH), 7.53 and 8.23 (two d's,4,J=8.5, ArH); mass spectrum m/e 306(M+), 264(M+-42), 237, 153, 125, 111, and 136.

Workup

  1. concentrationconcentrated under vacuum
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customTriturating the resulting oil with diethyl ether

Sources & evidence

ORD record
ord-1808abb5a26d4cd39d8fd7ef9b8042df
Source dataset
uspto-grants-1982_11
Patent number
US04357342

Reaction notes

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