Hydrogen Sulfide → 3-Ethyl-4-(4-p-nitrobenzyloxycarbonylaminobutyrylthio)-2-oxoazetidine

HRID 1710249Notes

Reaction equation

HRID 1710249 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.ClC(O[CH2:12][CH:13](C)C)=O.[N+:16]([C:19]1[CH:35]=[CH:34][C:22]([CH2:23][O:24][C:25]([NH:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=O)=[O:26])=[CH:21][CH:20]=1)([O-:18])=[O:17].[SH2:36].S(=O)(=O)(O)[OH:38]>C(Cl)Cl>[CH2:12]([CH:7]1[CH:4]([S:36][C:31](=[O:33])[CH2:30][CH2:29][CH2:28][NH:27][C:25]([O:24][CH2:23][C:22]2[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[CH:35][CH:34]=2)=[O:26])[NH:3][C:6]1=[O:38])[CH3:13]

Participants

7

Reactant 5

HCID 402Hydrogen SulfideHCID 1118Sulfuric AcidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 31025414-(p-Nitrobenzyloxycarbonyl)aminobutyric acid

Product 1

HCID 230357713-Ethyl-4-(4-p-nitrobenzyloxycarbonylaminobutyrylthio)-2-oxoazetidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In succession, 2.2 g (20 mmole) of triethylamine and a solution of 1.4 ml (10 mmole) of isobutyl chloroformate in 20 ml of dry methylene chloride are added dropwise to a solution, cooled to -10°, of 2.82 g (10 mmole) of 4-p-nitrobenzyloxycarbonylaminobutyric acid in 50 ml of dry methylene chloride. The reaction mixture is stirred for one hour and then a strong current of hydrogen sulphide is conveyed through for 2 hours. After acidifying with 2N sulphuric acid, the organic phase is separated off, dried and concentrated by evaporation in vacuo. The resulting 4-p-nitrobenzyloxycarbonylaminothiobutyric acid can be further processed without further purification.

Workup

  1. customis conveyed through for 2 hours
  2. customthe organic phase is separated off
  3. customdried
  4. concentrationconcentrated by evaporation in vacuo
  5. customThe resulting 4-p-nitrobenzyloxycarbonylaminothiobutyric acid can be further processed without further purification

Sources & evidence

ORD record
ord-43442238b72d4f999099f17e10cb0ebd
Source dataset
uspto-grants-1990_08
Patent number
US04952690

Reaction notes

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