HCID 11713948, compound → HCID 59571724, compound

HRID 2194310Notes

Reaction equation

HRID 2194310 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH2:31][C:32]1[N:33]=[C:34]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:35][C:36]=1[CH3:37])[CH2:6][N:7]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([O:20][C@@H:21]([CH2:25][CH3:26])[C:22]([OH:24])=[O:23])[C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2.C(C(CCCC)C([O-])=O)C.[Na+:54]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH2:31][C:32]1[N:33]=[C:34]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:35][C:36]=1[CH3:37])[CH2:6][N:7]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([O:20][C@@H:21]([CH2:25][CH3:26])[C:22]([O-:24])=[O:23])[C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2.[Na+:54]

Participants

4

Reactant 2

HCID 11713948HCID 11713948, compoundHCID 23672331Sodium 2-ethylhexanoate

Product 1

HCID 59571724HCID 59571724, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

420 mg of (S)-(+)-2-{9-[3-methoxy-4-(5-methyl-2-phenyl-oxazole-4-ylmethoxy)-benzyl]-9H-carbazole-4-yloxy}butyric acid was suspended in 4.2 mL of ethyl acetate, 125 mg of sodium 2-ethylhexanoate was added thereto, and refluxed for 1 hour. After cooling, the crystalline precipitate was isolated by filtration, washed with ethyl acetate, dried under reduced pressure, and 437 mg of the subject compound was prepared as white crystal. Optical purity 96% ee (HPLC).

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureAfter cooling
  3. customthe crystalline precipitate was isolated by filtration
  4. washwashed with ethyl acetate
  5. dry with materialdried under reduced pressure, and 437 mg of the subject compound
  6. customwas prepared as white crystal

Sources & evidence

ORD record
ord-c70ba5d8123741cdaf35160d65c48dc0
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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