Sodium Hydroxide → HCID 86722991, compound

HRID 1404385Notes

Reaction equation

HRID 1404385 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH3:24])[CH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]([O:21]CC)=[O:20])[CH2:14][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH3:24])[CH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]([OH:21])=[O:20])[CH2:14][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86722989HCID 86722989, compound

Product 1

HCID 86722991HCID 86722991, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[4-[2-(tert-butoxycarbonylamino)ethyl-methyl-amino]cyclohexyl]acetate (231 mg, 0.67 mmol) in methanol (2 mL) and THF (2 mL) was added NaOH (1 mL, 2M aqueous solution). The resulting solution was stirred for 2.75 hours then concentrated under reduced pressure to approximately ¼ the original volume. The residue was acidified with HCl (3 mL, 1M aqueous solution). This solution was purified directly by reverse phase silica chromatography (30 g of C18 silica; eluted with 5-100% acetonitrile/water/0.1% TFA) to give the title compound.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThis solution was purified directly by reverse phase silica chromatography (30 g of C18 silica; eluted with 5-100% acetonitrile/water/0.1% TFA)

Sources & evidence

ORD record
ord-cc806558a677491fa1c340bdfcd1de6b
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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