Sodium Hydroxide → HCID 59118164, compound

HRID 432120Notes

Reaction equation

HRID 432120 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:25][C@H:26]1[CH2:35][CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:36]([O:38]CC)=[O:37])[CH:32]=2)[O:27]1)[CH2:9][C@@H:10]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]2[CH3:24])=[CH:16][CH:17]=1)[OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C:6]([N:8]([CH2:25][C@H:26]1[CH2:35][CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:36]([OH:38])=[O:37])[CH:32]=2)[O:27]1)[CH2:9][C@@H:10]([C:12]1[CH:13]=[N:14][C:15]([N:18]2[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]2[CH3:24])=[CH:16][CH:17]=1)[OH:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59118126HCID 59118126, compound

Product 1

HCID 59118164HCID 59118164, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl (2R)-2-[((tert-butoxycarbonyl){(2R)-2-[6-(2,5-dimethyl-1H-pyrrol-1-yl)-3-pyridinyl]-2-hydroxyethyl}amino)methyl]-3,4-dihydro-2H-chromene-6-carboxylate (Example 359, 0.21 mmol, 1.0 eq.) and 1N NaOH (0.63 mmol, 3.0 eq.) in EtOH (2 mL) was heated to reflux for 1.5 hours. The reaction mixture was allowed to cool to room temperature and was concentrated in vacuo to afford a residue that was purified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, 100:5 CH2Cl2:MeOH). The product was obtained as a white foam in 72% yield. MH+=522.3, RT=3.11 min.

Workup

  1. temperatureto reflux for 1.5 hours
  2. concentrationwas concentrated in vacuo
  3. customto afford a residue that
  4. customwas purified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, 100:5 CH2Cl2:MeOH)
  5. customThe product was obtained as a white foam in 72% yield

Sources & evidence

ORD record
ord-d36a19e84d894e73968f424b18304302
Source dataset
uspto-grants-2003_12
Patent number
US06660752B2

Reaction notes

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