Hydrogen Sulfide → HCID 178523373, compound

HRID 462396Notes

Reaction equation

HRID 462396 reaction equation
C(N(CC)CC)C.ClC(OCC(C)C)=O.[N+:16]([C:19]1[CH:34]=[CH:33][C:22]([CH2:23][O:24][C:25]([NH:27][CH2:28][CH2:29][C:30](O)=[O:31])=[O:26])=[CH:21][CH:20]=1)([O-:18])=[O:17].S.[S:36](=O)(=O)(O)O>C(Cl)Cl>[N+:16]([C:19]1[CH:34]=[CH:33][C:22]([CH2:23][O:24][C:25]([NH:27][CH2:28][CH2:29][C:30]([OH:31])=[S:36])=[O:26])=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

7

Reactant 5

HCID 402Hydrogen SulfideHCID 1118Sulfuric AcidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 13175150HCID 13175150, compound

Product 1

HCID 178523373HCID 178523373, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.4 g (40 mmol) of triethylamine and a solution of 2.8 ml (2 mmol) of isobutyl chloroformate in 20 ml of dry methylene chloride are added dropwise, in succession, to a solution, cooled to -10°, of 5.36 g (20 mmol) of 3-p-nitrobenzyloxycarbonylaminopropionic acid in 100 ml of dry methylene chloride. The reaction mixture is stirred for one hour at -18°, then for 11/2 hours a strong current of hydrogen sulphide is passed through and the mixture allowed to heat up to room temperature. After acidifying with 2N sulphuric acid, again in the cold, the organic phase is separated, dried and concentrated in vacuo. The 3-p-nitrobenzyloxycarbonylaminothiopropionic acid obtained can be used without further purification.

Workup

  1. custom2 hours
  2. customagain in the cold, the organic phase is separated
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2cfdfc3e32348b083226b63a9aaeba2
Source dataset
uspto-grants-1985_05
Patent number
US04515717

Reaction notes

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