Methanol → HCID 56646832, compound

HRID 579179Notes

Reaction equation

HRID 579179 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:29]#[C:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:8][C:9]=1[N:10]1[C@H:15]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][O:13][C@@:12]([CH2:23][CH:24]([OH:27])[CH2:25][OH:26])([CH3:22])[C:11]1=[O:28])=[O:4].CO.O.O[Li].O>C1COCC1>[CH:16]1([C@H:15]2[N:10]([C:9]3[CH:8]=[C:7]([C:29]#[C:30][C:31]([CH3:34])([CH3:33])[CH3:32])[S:6][C:5]=3[C:3]([OH:4])=[O:2])[C:11](=[O:28])[C@:12]([CH2:23][CH:24]([OH:27])[CH2:25][OH:26])([CH3:22])[O:13][CH2:14]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66684550HCID 66684550, compound

Product 1

HCID 56646832HCID 56646832, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-[(2R,5R)-5-Cyclohexyl-2-(2,3-dihydroxy-propyl)-2-methyl-3-oxo-morpholin-4-yl]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester from the previous step was dissolved in 4.0 ml of THF and 0.3 mL of solution was taken out for the reaction. To the stirred solution was added THF (0.3 mL), MeOH (0.3 mL), water (0.3 mL), and LiOH.H2O (25.6 mg, 0.61 mmol, 10.0 equiv) and the resulting solution was stirred at room temperature for 30 minutes. The reaction was quenched by addition of 3.0 N HCl aqueous solution until pH=5. To the solution was then added EtOAc and the phases were separated. The aqueous layer was extracted by EtOAc. The organic layers were combined, dried (over Na2SO4) and concentrated. The residue was purified by HPLC (0.1% NH4OH, MeCN/H2O, 10%-90%) to give product (11 mg, 37.7% yield) as white solid. MS: 478 [M−H+].

Workup

  1. customThe reaction was quenched by addition of 3.0 N HCl aqueous solution until pH=5
  2. customadded EtOAc and the phases were separated
  3. extractionThe aqueous layer was extracted by EtOAc
  4. dry with materialdried (over Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by HPLC (0.1% NH4OH, MeCN/H2O, 10%-90%)

Sources & evidence

ORD record
ord-e6f512a4b56443c0a8f9f445eefb8792
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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