Sodium Hydroxide → HCID 50905947, compound

HRID 1046448Notes

Reaction equation

HRID 1046448 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[S:8][C:9]([C:34]#[C:35][C:36]([CH3:41])([CH3:40])[CH2:37][CH2:38][OH:39])=[CH:10][C:11]=1[N:12]([C:25]([CH:27]1[CH2:32][CH2:31][CH:30]([CH3:33])[CH2:29][CH2:28]1)=[O:26])[CH:13]1[CH2:18][CH2:17][CH:16]([O:19][CH:20]2[CH2:24][CH2:23][O:22][CH2:21]2)[CH2:15][CH2:14]1)=[O:6]>CO.C1COCC1>[OH:39][CH2:38][CH2:37][C:36]([CH3:40])([CH3:41])[C:35]#[C:34][C:9]1[S:8][C:7]([C:5]([OH:6])=[O:4])=[C:11]([N:12]([C:25]([CH:27]2[CH2:28][CH2:29][CH:30]([CH3:33])[CH2:31][CH2:32]2)=[O:26])[CH:13]2[CH2:14][CH2:15][CH:16]([O:19][CH:20]3[CH2:24][CH2:23][O:22][CH2:21]3)[CH2:17][CH2:18]2)[CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58113897HCID 58113897, compound

Product 1

HCID 50905947HCID 50905947, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaOH (0.500 mL of a 1.0 N aqueous solution) was added dropwise to a solution of 5-(5-hydroxy-3,3-dimethyl-pent-1-ynyl)-3-{(4-methyl-cyclohexanecarbonyl)-[4-(tetrahydro-furan-3-yloxy)-cyclohexyl]-amino}-thiophene-2-carboxylic acid methyl ester (157 mg, 0.28 mmol) in methanol (1.5 mL) and THF (1.5 mL) at room temperature. The reaction was stirred until TLC indicated that all of the starting material was consumed. The reaction was evaporated to dryness to give a solid residue that was purified by column chromatography on reverse phase C18 silica gel (100% water to 5% acetonitrile/water). Fractions containing product were pooled and evaporated to provide 5-(5-hydroxy-3,3-dimethyl-pent-1-ynyl)-3-{(4-methyl-cyclohexanecarbonyl)-[4-(tetrahydro-furan-3-yloxy)-cyclohexyl]-amino}-thiophene-2-carboxylic acid (Compound 314)(52 mg, 33%) as a solid. MS (m/z): 546.0 [M+H]+; HPLC retention time 3.75 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

Workup

  1. customwas consumed
  2. customThe reaction was evaporated to dryness
  3. customto give a solid residue that
  4. customwas purified by column chromatography on reverse phase C18 silica gel (100% water to 5% acetonitrile/water)
  5. additionFractions containing product
  6. customevaporated

Sources & evidence

ORD record
ord-1680a1afdba546a4be7663583a223921
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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