Methanethiol → HCID 14860708, compound

HRID 2256004Notes

Reaction equation

HRID 2256004 reaction equation
CCN(CC)CC.[C:8]([NH:11][CH:12](Br)[C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])(=[O:10])[CH3:9].[CH3:24][SH:25]>C1COCC1>[C:8]([NH:11][CH:12]([S:25][CH3:24])[C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 8471TriethylamineHCID 14860701HCID 14860701, compound

Product 1

HCID 14860708HCID 14860708, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A cooled (-78° C.) solution or Et3N (4.85 g, 48.0 mmol) in THF (20 mL) was added to a cooled (-78° C.) solution of 2-acetamido-N-benzyl-2-bromoacetamide (prepared from 2-acetamido-N-benzyl-2-ethoxyacetamide (4.00 g, 16.0 mmol) and BBr3 (1M in CH2Cl2, 20.0 mL, 20.0 mmol)) in THF (275 mL). A cooled (-78° C.) solution of excess MeSH (5-6 equiv) in THF (55 mL) was then added. The reaction mixture was stirred at this temperature (30 min) and then at room temperature (1 h). The insoluble materials were filtered and the filtrate was evaporated to dryness in vacuo. The oily residue obtained was purified by flash column chromatography on SiO2 gel (2% MeOH/CHCl3) to give 1.10 g (27%) of the desired product as a yellow orange oil. The product was purified by a second flash column chromatography on SiO2 gel (2% MeOH/CHCl3) to give 0.72 g of the pure product as a white solid.

Workup

  1. additionwas added to
  2. additionwas then added
  3. customat room temperature
  4. custom(1 h)
  5. filtrationThe insoluble materials were filtered
  6. customthe filtrate was evaporated to dryness in vacuo
  7. customThe oily residue obtained
  8. customwas purified by flash column chromatography on SiO2 gel (2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-a5b8ea4c94a24de0b26eaa7cccf4fb22
Source dataset
uspto-grants-1997_08
Patent number
US05654301

Reaction notes

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