Methanol → HCID 59505398, compound

HRID 1193262Notes

Reaction equation

HRID 1193262 reaction equation
O=S(Cl)Cl.Cl.[NH2:6][C@H:7]1[C:15]2[C:10](=[CH:11][C:12]([F:19])=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=2)[CH2:9][CH2:8]1.[CH3:20]O>>[NH2:6][C@H:7]1[C:15]2[C:10](=[CH:11][C:12]([F:19])=[C:13]([C:16]([O:18][CH3:20])=[O:17])[CH:14]=2)[CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 66799216(R)-3-amino-6-fluoro-2,3-dihydro-1H-indene-5-carboxylic acid hydrochloride

Product 1

HCID 59505398HCID 59505398, compoundYield 89%

Procedure

SOCl2 (0.75 ml, 10.365 mmol, 2.4 eq) was added dropwise at 0° C., with stirring, to a suspension of (R)-3-amino-6-fluoro-2,3-dihydro-1H-indene-5-carboxylic acid hydrochloride (commercially available from NetChem (Order No. 573243)) (1 g, 4.319 mmol, 1 eq) in methanol (20 ml). The reaction mixture was stirred for 14 h at room temperature. When the reaction was complete according to TLC monitoring, concentration under reduced pressure was carried out and the residue was diluted with saturated sodium hydrogen carbonate solution (50 ml) and extracted with 10% methanol/dichloromethane (100 ml). The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The desired product was in the form of a light-green solid. Yield: 89% (800 mg, 3.827 mmol)

Workup

  1. concentrationWhen the reaction was complete according to TLC monitoring, concentration under reduced pressure
  2. additionthe residue was diluted with saturated sodium hydrogen carbonate solution (50 ml)
  3. extractionextracted with 10% methanol/dichloromethane (100 ml)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c2f007b25e824250961329446fa2afbe
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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