HCID 178472777, compound → HCID 178525922, compound

HRID 574669Notes

Reaction equation

HRID 574669 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][NH:6][C:7]([C:9]1[N:14]=[C:13]([OH:15])[C:12]([C:16](=[O:29])[NH:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)=[CH:11][N:10]=1)=[O:8])C>[OH-].[K+]>[OH:15][C:13]1[C:12]([C:16](=[O:29])[NH:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)=[CH:11][N:10]=[C:9]([C:7]([NH:6][CH2:5][C:4]([OH:30])=[O:3])=[O:8])[N:14]=1

Participants

3

Reactant 1

HCID 178472777HCID 178472777, compound

Product 1

HCID 178525922HCID 178525922, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

Compound 2-20 (300 mg, 0.67 mmol) was added to a 10% KOH solution (30 mL) and stirred at 50° C. for 30 min, then cooled to room temperature, washed with DCM (30 mL×2). The aqueous phase was acidified with 5% HCl to pH 23 and filtrated and dried to afford compound 2-21 as a white solid (200 mg, 79%). 1H NMR (300 MHz, DMSO-d6): δ 3.92-3.94 (d, J=6.0 Hz, 2H), 5.0-5.01 (d, J=3.0 Hz, 2H), 7.48-7.54 (m, 4H), 7.55-7.57 (m, 3H), 8.44 (br s, 1H), 9.40 (m, 1H), 9.93 (br s, 1H), 12.80 (br s, 1H), 13.56 (br s, 1H). LC-MS: (M−H)− 379.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with DCM (30 mL×2)
  3. filtrationfiltrated
  4. customdried

Sources & evidence

ORD record
ord-d3d487e2b8c54bc491f4991f7747a220
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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