Hydrogen Sulfide → HCID 178523349, compound

HRID 1248422Notes

Reaction equation

HRID 1248422 reaction equation
C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=O)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.S.[S:34](=O)(=O)(O)O>C(Cl)Cl>[CH2:16]([O:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[S:34])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 402Hydrogen SulfideHCID 1118Sulfuric AcidHCID 8471TriethylamineHCID 211844-(((Benzyloxy)carbonyl)amino)butanoic acidHCID 62365Isobutyl chloroformate

Product 1

HCID 178523349HCID 178523349, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.2 g (20 mmol) of triethylamine and a solution of 1.4 ml (10 mmol) of isobutyl chloroformate in 20 ml of dry methylene chloride are added dropwise, in succession, to a solution, cooled to -10°, of 2.37 g (10 mmol) of 4-benzyloxycarbonylaminobutyric acid in 50 ml of dry methylene chloride. The reaction mixture is stirred for one hour at -10° and then a strong current of hydrogen sulphide is passed through for 11/2 hours. After warming to room temperature, the mixture is cooled again and acidified with 2N sulphuric acid. The organic phase is separated, dried and concentrated in vacuo. The 4-benzyloxycarbonylaminothiobutyric acid obtained can be used without further purification.

Workup

  1. custom2 hours
  2. temperaturethe mixture is cooled again
  3. customThe organic phase is separated
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7700fa081d1849a7a89cebeafe28e2db
Source dataset
uspto-grants-1985_06
Patent number
US04524028

Reaction notes

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