Sodium Hydroxide → HCID 118061507, compound

HRID 920837Notes

Reaction equation

HRID 920837 reaction equation
[I:1][C:2]1[C:19]([C:20]([O:22]CC)=[O:21])=[C:5]2[CH2:6][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:8]3([CH2:11][CH2:10]3)[CH2:9][N:4]2[N:3]=1.[OH-].[Na+]>C(O)C.O>[C:15]([O:14][C:12]([N:7]1[C:8]2([CH2:10][CH2:11]2)[CH2:9][N:4]2[N:3]=[C:2]([I:1])[C:19]([C:20]([OH:22])=[O:21])=[C:5]2[CH2:6]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118071145HCID 118071145, compound

Product 1

HCID 118061507HCID 118061507, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of Intermediate 350D (0.500 g, 1.118 mmol) in ethanol (10 mL) and water (1 mL) was added NaOH (0.369 g, 9.21 mmol) and the resulting solution was stirred at RT for 12 h. The volatiles were removed under reduced pressure and the residue was acidified with an aqueous solution of 1.5 N HCl. The solid product separated was filtered through a Buchner funnel and dried under vacuum to afford Intermediate 350E as a white solid (0.43 g, 90%). MS(ES): m/z=420 [M+H]+; 1H NMR (400 MHz, chloroform-d) δ ppm 6.19 (br. s., 1H), 4.92 (br. s., 2H), 4.06 (br. s., 2H), 1.48 (s, 9H), 1.19 (br. s., 2H), 1.01-0.83 (m, 2H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customThe solid product separated
  3. filtrationwas filtered through a Buchner funnel
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8fca123c09cb471781a2e167464fd74f
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

Loading…