Methanol → HCID 67563677, compound

HRID 583430Notes

Reaction equation

HRID 583430 reaction equation
S(Cl)([Cl:3])=O.Cl.[CH3:6][NH:7][CH:8]([CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:9][C:10]([OH:12])=[O:11].[CH3:26]O>>[ClH:3].[CH3:26][O:11][C:10](=[O:12])[CH2:9][CH:8]([NH:7][CH3:6])[CH:13]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 67564201HCID 67564201, compound

Product 1

HCID 67563677HCID 67563677, compound

Procedure

3 ml (40.9 mmol) of thionyl chloride are added dropwise at 0° C. to a fine suspension of 6.2 g (20.4 mmol) of 3-methylamino-4,4-diphenyl-butyric acid hydrochloride in 70 ml of methanol. After a total of 88 hours at room temperature the reaction mixture is concentrated by evaporation and ether is added. The beige precipitate is filtered off, then washed with ether and dried under a high vacuum. The title compound is obtained in the form of a beige solid. Rt (HPLC)=11.2 min; 1H-NMR (300 MHz, d6 -DMSO, RT) d 9.41 (br, 1H), 8.56 (br, 1H), 7.59-7.18 (m, 10H), 4.56 (m, 1H), 4.43 (d, 1H), 3.46 (s, 3H), 2.87 (dd, 1H), 2.64 (dd,1H), 2.40 (s, 3H).

Workup

  1. concentrationAfter a total of 88 hours at room temperature the reaction mixture is concentrated by evaporation and ether
  2. additionis added
  3. filtrationThe beige precipitate is filtered off
  4. washwashed with ether
  5. customdried under a high vacuum

Sources & evidence

ORD record
ord-798cc1ec92cb45b69eae2875325e91e4
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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