Sodium Hydroxide → HCID 178434841, compound

HRID 632944Notes

Reaction equation

HRID 632944 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:39])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:38])[CH2:21][CH2:22][NH:23][C:24]([C:26]3[N:27]=[C:28]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:29][C:30]=3[CH3:31])=[O:25])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1>C1COCC1.CO.O>[CH3:31][C:30]1[O:29][C:28]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[N:27][C:26]=1[C:24]([NH:23][CH2:22][CH2:21][C:20]([NH:19][C:16]1[CH:15]=[CH:14][C:13]([C@H:10]2[CH2:9][CH2:8][C@H:7]([CH2:6][C:5]([OH:39])=[O:4])[CH2:12][CH2:11]2)=[CH:18][CH:17]=1)=[O:38])=[O:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178500676HCID 178500676, compound

Product 1

HCID 178434841HCID 178434841, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
25 °C

Procedure

NaOH (59.6 mg, 1.5 mmol) was added to trans-[4-(4-{3-[(5-methyl-2-phenyloxazole-4-carbonyl)amino]propionylamino}phenyl)cyclohexyl]acetic acid methyl ester (75 mg, 0.15 mmol) dissolved in THF/MeOH/water (20 mL, 3:2:1). The reaction mixture was stirred at 25° C. for 5 hours and concentrated under vacuum. The residue was acidified with 1M HCl up to pH 2 and extracted with ethyl acetate. The extract was washed with brine and dried with anhydrous sodium sulfate and concentrated under vacuum. The residue was stirred with acetonitrile and filtered, then eluted with a gradient of methanol/DCM (5-10%) on a silica gel by column chromatography and purified. Therefore, the desired compound as a white solid was obtained.

Workup

  1. concentrationconcentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. stirringThe residue was stirred with acetonitrile
  7. filtrationfiltered
  8. washeluted with a gradient of methanol/DCM (5-10%) on a silica gel by column chromatography
  9. custompurified

Sources & evidence

ORD record
ord-34b537a59b90401b9679db7e4b68ffce
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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