(S)-mandelic acid → HCID 70239495, compound

HRID 565724Notes

Reaction equation

HRID 565724 reaction equation
[CH3:1][C@H:2]([N:9]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:10]1[C:11]([O:13][CH3:14])=[O:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:19]([OH:29])(=[O:28])[C@H:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[OH:21]>C(OC)(C)(C)C>[C:19]([OH:29])(=[O:28])[C@H:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[OH:21].[CH3:1][C@H:2]([N:9]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:10]1[C:11]([O:13][CH3:14])=[O:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 439616(S)-mandelic acidHCID 70239410HCID 70239410, compound

Product 2

HCID 439616(S)-mandelic acidHCID 70239495HCID 70239495, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

Methyl N-[(S)-α-methylbenzyl]-(RS)-pipecolate (157 mg) was dissolved in methyl tert-butyl ether (2 ml) at room temperature. To this solution was added a mixture of L-(+)-mandelic acid (86 mg) and methyl tert-butyl ether (2 ml) at room temperature and stirred. The resulting solution was allowed to stand at −20° C. for one day to form a crystal. The crystals were separated by filtration and dried to yield an L-(+)-mandelic acid salt of methyl N-[(S)-α-methylbenzyl]-(S)-pipecolate (79.9 mg) in an optical purity of 73% de and a yield of 23%.

Workup

  1. additionTo this solution was added
  2. customto form a crystal
  3. customThe crystals were separated by filtration
  4. customdried

Sources & evidence

ORD record
ord-a781dfaa67ff4b8f983fabb696471456
Source dataset
uspto-grants-2001_01
Patent number
US06172234B2

Reaction notes

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