HCID 178469787, compound → HCID 178524758, compound

HRID 574660Notes

Reaction equation

HRID 574660 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([OH:16])[C:13]([C:17]([O:19]CC)=[O:18])=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[K+]>[CH2:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([OH:16])[C:13]([C:17]([OH:19])=[O:18])=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 178469787HCID 178469787, compound2×

Product 1

HCID 178524758HCID 178524758, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A mixture of step C product (2-d) (10.0 g, crude) in a 3% KOH solution (200 mL) was stirred at 70° C. for 1 h, then cooled to room temperature. The material then washed with DCM (200 mL×2). The aqueous phase was acidified with 5% HCl to pH 1˜2, filtrated and then dried to afford product as a white solid (2-e) (6.2 g, 95% for 2 steps). 1H NMR (300 MHz, CD3OD): δ4.56 (s, 2H), 4.72 (s, 2H), 7.33-7.40 (m, 5H), 8.61 (s, 1H), LC-MS: (M+H)+ 261.

Workup

  1. washThe material then washed with DCM (200 mL×2)
  2. filtrationfiltrated
  3. customdried

Sources & evidence

ORD record
ord-55a028c6aac046718b95400de4cbfb11
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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