Methanol → HCID 20516936, compound

HRID 2199044Notes

Reaction equation

HRID 2199044 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([C:15]([OH:17])=[O:16])[NH:8][CH2:7][CH2:6][C:5]2=1.S(Cl)([Cl:20])=O.[CH3:22]O>>[ClH:20].[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([C:15]([O:17][CH3:22])=[O:16])[NH:8][CH2:7][CH2:6][C:5]2=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 12773710HCID 12773710, compound

Product 1

HCID 20516936HCID 20516936, compound

Conditions

Temperature
0 °C

Procedure

The title compound was prepared by mixing 6-fluoro-1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid (2 g; 0.0085 mole) with 60 ml of methanol. After cooling at 0° C., thionyl chloride (2 ml., 0.028 mole) was added dropwise and the mixture stirred at room temperature for 24 hours whereupon the solvent was removed in vacuo. The residue was partitioned in ethylacetate/6% K2CO3 solution whereupon the organic phase was dried over MgSO4, filtered and treated with 4 N HCl in dioxane to pH 5. A white solid product was collected. Yield: 1.2 g (38%) MP 219°-220° C.

Workup

  1. customwas removed in vacuo
  2. customThe residue was partitioned in ethylacetate/6% K2CO3 solution whereupon the organic phase
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. additiontreated with 4 N HCl in dioxane to pH 5
  6. customA white solid product was collected

Sources & evidence

ORD record
ord-9cfee5c6f31e4be9978cb0daa8daa4ef
Source dataset
uspto-grants-1982_11
Patent number
US04361566

Reaction notes

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