HCID 178472778, compound → HCID 178525923, compound

HRID 574666Notes

Reaction equation

HRID 574666 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:16][C:17]([C:19]2[C:20]([OH:34])=[N:21][C:22]([C:25]([NH:27][CH2:28][C:29]([O:31]CC)=[O:30])=[O:26])=[N:23][CH:24]=2)=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1>[OH-].[K+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:16][C:17]([C:19]2[C:20]([OH:34])=[N:21][C:22]([C:25]([NH:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[N:23][CH:24]=2)=[O:18])[C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 178472778HCID 178472778, compound

Product 1

HCID 178525923HCID 178525923, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

To a 10% KOH solution (30 mL) was added compound 2-18 (53 mg, 0.11 mmol), and the mixture was stirred at 50° C. for 30 min, then cooled to room temperature. The cooled mixture was washed with DCM (30 mL×2). The aqueous phase was acidified with 5% HCl to about a pH 2˜3, filtrated and dried to afford compound 2-19 as a white solid (42 mg, 85%). 1H NMR (300 MHz, DMSO-d6): δ 3.92-3.95 (d, J=9.0 Hz, 2H), 6.28-6.31 (d, J=9.0 Hz, 2H), 7.18-7.34 (m, 8H), 8.47 (s, 1H), 9.36-9.39 (m, 1H), 10.33 (br s, 1H). LC-MS: (M+Na)+ 465.

Workup

  1. temperaturecooled to room temperature
  2. washThe cooled mixture was washed with DCM (30 mL×2)
  3. filtrationfiltrated
  4. customdried

Sources & evidence

ORD record
ord-77afe7ff1b4e427f8e4337c1071b0075
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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