Formic Acid → HCID 21269030, compound

HRID 1194997Notes

Reaction equation

HRID 1194997 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]N2CC(C(O)C)C2=O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)=[O:37].[N:39]([C:46](OCC)=O)=NC(OCC)=O.[O:51]1[CH2:55][CH2:54][CH2:53][CH2:52]1>CO.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH:46]2[NH:39][C:55](=[O:51])[CH:54]2[CH:53]([OH:37])[CH3:52])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 284Formic AcidHCID 8028Tetrahydrofuran2×HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 131715912HCID 131715912, compound

Product 1

HCID 21269030HCID 21269030, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

617 mg (2.39 mmol) of rac-(αS*,3S*,4R*)-4-[(p-chlorophenyl)thio-3-(1-hydroxyethyl)-2-azetidinone in 30 ml of tetrahydrofuran are treated with 1.25 g (4.8 mmol) of triphenylphosphine and 0.18 ml (4.8 mmol) of formic acid. A solution of 1.1 g (4.8 mmol) of diethyl azodicarboxylate in 10 ml of tetrahydrofuran is slowly added dropwise thereto, the reaction mixture is stirred at room temperature for 2 hours, evaporated and the residue is filtered through silica gel (hexane/ethyl acetate). The oil obtained (680 mg) is dissolved in 30 ml of methanol, the solution is treated with 3 drops of concentrated hydrochloric acid, left to stand at room temperature for 2 hours and evaporated. The residue is filtered through silica gel (hexane/ethyl acetate). There is obtained rac--(αR*,3S*,4R*)-4-[(p-chlorophenyl)thio]-3-(1-hydroxyethyl)-2-azetidinone of melting point 130° ; IR 1760 cm-1.

Workup

  1. customevaporated
  2. filtrationthe residue is filtered through silica gel (hexane/ethyl acetate)
  3. customThe oil obtained (680 mg)
  4. waitleft
  5. waitto stand at room temperature for 2 hours
  6. customevaporated
  7. filtrationThe residue is filtered through silica gel (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ee8fa5f201234986b6ad1b219c5faf3b
Source dataset
uspto-grants-1989_03
Patent number
US04816581

Reaction notes

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