Methanol → HCID 66578492, compound

HRID 1528899Notes

Reaction equation

HRID 1528899 reaction equation
C([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]([O:37][CH2:38][CH3:39])[CH2:28][CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])C.CO.[OH-].[Na+]>C1COCC1>[CH2:38]([O:37][CH:27]([C:22]1[C:23]([CH3:26])=[N:24][O:25][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:11]=[CH:10][C:9]([C:6]3([C:4]([OH:5])=[O:3])[CH2:8][CH2:7]3)=[CH:14][CH:13]=2)=[CH:16][CH:17]=1)[CH2:28][CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH3:39]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 66578671HCID 66578671, compound

Product 1

HCID 66578492HCID 66578492, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

1-{4′-[4-(1-Ethoxy-4-phenyl-butyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester (0.070 g, 0.133 mmol) was dissolved in THF (3 mL) and MeOH (0.3 mL) then NaOH (3 N aq., 0.150 mL) was added. The reaction was heated to 70° C. overnight then an additional portion of NaOH (3 N aq., 0.150 mL) was added and the reaction was heated overnight again. After cooling the reaction was submitted to standard aqueous workup then purified by preparatory HPLC to afford a separable mixture of products, of which the major product was the title compound.

Workup

  1. temperaturethe reaction was heated overnight again
  2. temperatureAfter cooling the reaction
  3. customthen purified by preparatory HPLC
  4. customto afford
  5. additiona separable mixture of products

Sources & evidence

ORD record
ord-f6b004600508417a981bb5a59cb8432a
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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