2,2-Dimethylpropanethiol → HCID 59828882, compound

HRID 1191058Notes

Reaction equation

HRID 1191058 reaction equation
C[O-].[Na+].[CH3:4][C:5]([CH3:9])([CH3:8])[CH2:6][SH:7].[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]1[CH:20]=[N:21][C:22]([CH2:25]Cl)=[CH:23][CH:24]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CO.O.C(OCC)(=O)C>[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]1[CH:20]=[N:21][C:22]([CH2:25][S:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH3:4])=[CH:23][CH:24]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 3

HCID 742982,2-DimethylpropanethiolHCID 10942334Sodium MethoxideHCID 59828819HCID 59828819, compound

Product 1

HCID 59828882HCID 59828882, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, add sodium methoxide (630 mg, 3.51 mmol, 30% w/w in methanol) to a stirring mixture of 2,2-dimethyl-propane-1-thiol (365 mg, 3.51 mmol) and methanol (10 mL) at room temperature and stir for 30 min. Add 3-(tert-butoxycarbonylamino-methyl)-6-chloromethyl-pyridine (450 mg, 1.76 mmol) in methanol (5 mL) and stir the mixture for 2 h. Dilute the mixture with water and ethyl acetate. Separate the layers and extract the aqueous layer with ethyl acetate. Wash the combined organic extracts with water and brine. Dry the organic phase over Na2SO4, filter, and concentrate in vacuo to obtain the desired intermediate suitable for use without additional purification. MS (APCI+) m/z: 325 (M+H)+.

Workup

  1. customSeparate the layers
  2. extractionextract the aqueous layer with ethyl acetate
  3. washWash the combined organic extracts with water and brine
  4. dry with materialDry the organic phase over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-d08dcbb628c84862a4f4dfcc0f5ce29c
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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