Hydrogen Sulfide → HCID 178523373, compound

HRID 543593Notes

Reaction equation

HRID 543593 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 l 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 2 N 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-cc43094f25b44dbf84f0563e194f99f6
Source dataset
uspto-grants-1984_05
Patent number
US04447360

Reaction notes

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