Thionyl Chloride → HCID 20347463, compound

HRID 1701269Notes

Reaction equation

HRID 1701269 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([S:9][CH:10]1[N:13]([CH:14](O)[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])[C:12](=[O:29])[CH2:11]1)=[O:8].S(Cl)([Cl:32])=O>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([S:9][CH:10]1[N:13]([CH:14]([Cl:32])[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])[C:12](=[O:29])[CH2:11]1)=[O:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 20347460HCID 20347460, compound

Product 1

HCID 20347463HCID 20347463, compound

Procedure

To 800 mg. of p-nitrobenzyl 2-[4-(2-methoxyethoxyacetylthio)-2-oxo-1-azetidinyl]-2-hydroxyacetate was added (all at once) at 0° under N2 atmosphere, thionyl chloride (3 ml.) and the mixture was stirred at room temperature under N2 for 1 hour. The excess of thionyl chloride was removed in vacuo and the residue dissolved in dry benzene (10 ml.) and evaporated to dryness. There was obtained the title product (791 mg.) as a yellowish oil. nmr (CDCl3): δppm 2.9-3.9 (2H, m, H-3), 4.10 (3H, s, --OCH3), 3.5-3.9 (4H, m, --OCH2CH2O--), 4.24 (2H, s, O=C--CH2O--), 5.35-5.45 (2H, m, --CH2 --Ar), 5.70 (1H, m, H-4), 6.12 (1H, s, --CHCl), 7.52, 7.67, 8.21, 5.39 (4H, A2 ' B2 ', aromatic --H); ir (neat): 1780 cm-1 (broad, γc=o, β-lactam and ester), 1695 (γc=o, thioester), 1525 (γNO2).

Workup

  1. customThe excess of thionyl chloride was removed in vacuo
  2. dissolutionthe residue dissolved in dry benzene (10 ml.)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-2d7441152cb046ff9f843c0455e7b7c1
Source dataset
uspto-grants-1980_03
Patent number
US04192801

Reaction notes

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