N-(tert-butoxycarbonyl)-2-aminoethanethiol → HCID 20295353, compound

HRID 1389770Notes

Reaction equation

HRID 1389770 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][SH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:12]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20]Br)[CH2:16][CH2:15]1)=[O:13]>CO.[OH-].[K+]>[CH:12]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][S:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:16][CH2:15]1)=[O:13]

Participants

5

Reactant 2

HCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiolHCID 19812293N-Formyl-4-bromomethylpiperidine

Product 1

HCID 20295353HCID 20295353, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 14797Potassium HydroxideSolvent

Procedure

To a solution of (A) (5.3 g, 0.03 mole) in methanol (10 ml), 5 N potassium hydroxide in methanol (5 ml) was added, followed by N-formyl-4-bromomethylpiperidine (5.2 g, 0.025 mole). The mixture was left at room temperature for 20 hours. After removal of the solvent in vacuo, the residue was diluted with ether (50 ml) and filtered. The filtrate was washed with two 5 ml portions of 2 N sodium hydroxide, followed by water and dried. The solvent was stripped in vacuo, and the residue was chromatographed on silica gel (100 g), eluting with ether to give (B) as a colourless oil.

Workup

  1. customAfter removal of the solvent in vacuo
  2. additionthe residue was diluted with ether (50 ml)
  3. filtrationfiltered
  4. washThe filtrate was washed with two 5 ml portions of 2 N sodium hydroxide
  5. customdried
  6. customthe residue was chromatographed on silica gel (100 g)
  7. washeluting with ether

Sources & evidence

ORD record
ord-567d81fe96a14c83a7c40d9c8471df5d
Source dataset
uspto-grants-1981_01
Patent number
US04246262

Reaction notes

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