2-Propanethiol → HCID 58801857, compound

HRID 1364178Notes

Reaction equation

HRID 1364178 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C(N(CC)CC)C.[CH3:20][CH:21]([SH:23])[CH3:22]>CN(C)C=O>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][S:23][CH:21]([CH3:22])[CH3:20])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 8471TriethylamineHCID 62576Benzyl bromoacetate

Product 1

HCID 58801857HCID 58801857, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To benzyl bromoacetate (100 mg, 0.437 mmol) in dimethyl formamide (2 mL) is added triethylamine (67 uL, 0.481 mmol) and 2-propanethiol (41 uL, 0.437 mmol). After stirring at rt during 2 h, the solvent is evaporated, the residue is treated with dichloromethane and water. The organic phase is dried and evaporated to give a crude compound before purification by preparative HPLC (Column Waters C18 ODB 5 μm 19×50, Gradient: 0-2.5 min 5% ACN, 2.5-12.5 min 5-100% ACN, 12.5-15 min 100% ACN) to yield the title compound.

Workup

  1. customthe solvent is evaporated
  2. additionthe residue is treated with dichloromethane and water
  3. customThe organic phase is dried
  4. customevaporated
  5. customto give a crude compound
  6. custombefore purification by preparative HPLC (Column Waters C18 ODB 5 μm 19×50, Gradient: 0-2.5 min 5% ACN, 2.5-12.5 min 5-100% ACN, 12.5-15 min 100% ACN)

Sources & evidence

ORD record
ord-2a0ee6ab27bd4007acb56185088e96b1
Source dataset
uspto-grants-2011_02
Patent number
US07888351B2

Reaction notes

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