Sodium Hydroxide → HCID 58778919, compound

HRID 1372612Notes

Reaction equation

HRID 1372612 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C@H:22]3[CH2:26][O:27][CH:28]3[CH2:33][CH2:32][CH:31]([C:34]([O:36]C)=[O:35])[CH2:30][CH2:29]3)=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C@H:22]3[CH2:26][O:27][CH:28]3[CH2:29][CH2:30][CH:31]([C:34]([OH:36])=[O:35])[CH2:32][CH2:33]3)=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58778867HCID 58778867, compound

Product 1

HCID 58778919HCID 58778919, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

In THF (10 ml) and methanol (5 ml) was dissolved methyl 4-(1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-(2S)-pyrrolidinylmethoxy)cyclohexanecarboxylate (580 mg, 1.1 mmol), that is, a mixture of two diastereomers (cis and trans forms). After addition of 1N NaOH (1.5 ml, 1.5 mmol), the mixture was stirred at 70° C. for 24 hours. The residue obtained by distilling off the solvent under reduced pressure, was acidified weakly with 1N HCl. The crystals thus precipitated were collected by filtration under reduced pressure. The resulting crystals were washed with water and dried under reduced pressure, whereby 4-(1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-(2S)-pyrrolidinylmethoxy)cyclohexanecarboxylic acid was obtained as a mixture of two diasteromers. The mixture was separated by HPLC (C18 column, eluting with 0.02N acetate buffer-acetonitrile (1:1, v/v)), whereby Isomer A (150 mg, 27%) was obtained as a white crystalline solid.

Workup

  1. additiona mixture of two diastereomers (cis and trans forms)
  2. customThe residue obtained
  3. distillationby distilling off the solvent under reduced pressure
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration under reduced pressure
  6. washThe resulting crystals were washed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-72dc8c6047034c94811b32296ab65cfb
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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