Methanol → HCID 68001175, compound

HRID 932220Notes

Reaction equation

HRID 932220 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH:32]3[CH2:34][CH2:33]3)[CH2:22][NH:23][S:24]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)(=[O:26])=[O:25])[C:11](=[O:35])[C@:10]([CH2:37][C:38]([O:40]C)=[O:39])([CH3:36])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.CO.C1COCC1.[Li+].[OH-]>O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[C@@H:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C@@H:21]([CH:32]3[CH2:33][CH2:34]3)[CH2:22][NH:23][S:24]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)(=[O:26])=[O:25])[C:11](=[O:35])[C@:10]([CH2:37][C:38]([OH:40])=[O:39])([CH3:36])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67999458HCID 67999458, compound

Product 1

HCID 68001175HCID 68001175, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-cyclopropyl-2-(thiophene-2-sulfonamido)ethyl)-3-methyl-2-oxopiperidin-3-yl)acetate (30 mg, 0.048 mmol; Example 263, Step D) in a mixture of water (0.16 mL), MeOH (0.16 mL), and THF (0.16 mL) was added 2 M aq. LiOH (48 μL, 0.095 mmol) at rt and the resulting solution was stirred at rt for 5 h. The reaction was quenched (sat. NH4Cl), extracted (2×EtOAc), and washed (brine). The combined organic layers were dried (Na2SO4) and concentrated under the reduced pressure. Purification of the residue by chromatography on silica gel (12 g SiO2, gradient elution of 50% to 100% EtOAc in Hex and 30% iPrOH/DCM) provided the title compound as a white powder.

Workup

  1. customThe reaction was quenched (sat. NH4Cl)
  2. extractionextracted (2×EtOAc)
  3. washwashed (brine)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under the reduced pressure
  6. customPurification of the residue by chromatography on silica gel (12 g SiO2, gradient elution of 50% to 100% EtOAc in Hex and 30% iPrOH/DCM)

Sources & evidence

ORD record
ord-53e3973fca9047e7b12909997d2abc36
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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