Methanol → HCID 178442400, compound

HRID 244922Notes

Reaction equation

HRID 244922 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:27]#[C:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].CO.O.O[Li].O>C1COCC1>[CH3:31][C:29]([CH3:30])([CH3:32])[C:28]#[C:27][C:7]1[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]([N:10]([C@H:20]2[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]2)[C:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]2)=[O:12])[CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 178499344HCID 178499344, compound

Product 1

HCID 178442400HCID 178442400, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

5-(3,3-Dimethyl-but-1-ynyl)-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexane-carbonyl)-amino]-thiophene-2-carboxylic acid methyl ester is dissolved in a 3:2:1 mixture of THF:methanol:H2O and treated with a 1N solution of LiOH.H2O. After 2 h of stirring at 60° C., the reaction mixture is concentrated under reduced pressure on a rotary evaporator. The mixture is partitioned between ethyl acetate and water. The water layer is acidified using 0.1 N HCl. The EtOAc layer is separated and dried over Na2SO4. The solvent is removed and the residue is purified by column chromatography using methanol and dichloromethane (1:9) as eluent to obtain the title compound.

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure on a rotary evaporator
  2. customThe mixture is partitioned between ethyl acetate and water
  3. customThe EtOAc layer is separated
  4. dry with materialdried over Na2SO4
  5. customThe solvent is removed
  6. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-b52206718b5b41cb88103a0d5adc1276
Source dataset
uspto-grants-2014_02
Patent number
US08658674B2

Reaction notes

Loading…