(R)-(-)-Methyl mandelate → HCID 54285107, compound

HRID 1489170Notes

Reaction equation

HRID 1489170 reaction equation
COC(=O)[C@@H](C1C=CC=CC=1)O.[NH2:13][CH2:14][C:15]1([CH2:41][F:42])[CH2:19][CH2:18][N:17]([C:20]2[C:29]([O:30][CH3:31])=[C:28]3[C:23]([C:24](=[O:39])[C:25]([C:35]([O:37][CH3:38])=[O:36])=[CH:26][N:27]3[CH:32]3[CH2:34][CH2:33]3)=[CH:22][C:21]=2[F:40])[CH2:16]1>CO>[NH2:13][CH2:14][C@@:15]1([CH2:41][F:42])[CH2:19][CH2:18][N:17]([C:20]2[C:29]([O:30][CH3:31])=[C:28]3[C:23]([C:24](=[O:39])[C:25]([C:35]([O:37][CH3:38])=[O:36])=[CH:26][N:27]3[CH:32]3[CH2:34][CH2:33]3)=[CH:22][C:21]=2[F:40])[CH2:16]1

Participants

4

Reactant 2

HCID 2724623(R)-(-)-Methyl mandelateHCID 22903657HCID 22903657, compound

Product 1

HCID 54285107HCID 54285107, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of (R)-O-methylmandelic acid (2.2 g) in methanol (8 ml) was added to a solution of the compound (8.1 g) obtained in Example 2 in methanol (32 ml), and the mixture was left standing at room temperature for 3 days. The precipitated crystals were collected by filtration and recrystallized 4 times from methanol. The obtained crystals were suspended in water, and the suspension was made alkaline with potassium carbonate and extracted with chloroform. The extract was washed with water, dried and concentrated to give 1.1 g of the object compound, melting point 150°-152° C., optical purity not less than 95% ee (HPLC).

Workup

  1. waitthe mixture was left
  2. filtrationThe precipitated crystals were collected by filtration
  3. customrecrystallized 4 times from methanol
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c5902a11ee61438ab70b37678f0dff21
Source dataset
uspto-grants-1997_10
Patent number
US05677316

Reaction notes

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