Sodium Hydroxide → HCID 45380845, compound

HRID 1911288Notes

Reaction equation

HRID 1911288 reaction equation
[CH3:1][C:2]1([CH3:34])[CH2:11][C@@H:10]([NH:12][C:13](=[O:29])[NH:14][C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[CH:17]=[C:18]([NH:25]C(=O)C)[N:19]=[CH:20]3)[C:9]2[C:4](=[CH:5][C:6]([C:30]([F:33])([F:32])[F:31])=[CH:7][CH:8]=2)[O:3]1.[OH-].[Na+]>CO.O>[NH2:25][C:18]1[N:19]=[CH:20][C:21]2[C:16]([CH:17]=1)=[C:15]([NH:14][C:13]([NH:12][C@H:10]1[C:9]3[C:4](=[CH:5][C:6]([C:30]([F:33])([F:31])[F:32])=[CH:7][CH:8]=3)[O:3][C:2]([CH3:34])([CH3:1])[CH2:11]1)=[O:29])[CH:24]=[CH:23][CH:22]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68596526HCID 68596526, compound

Product 1

HCID 45380845HCID 45380845, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of Example 90D (505 mg, 1.07 mmol) and NaOH (428 mg, 10.7 mmol) in MeOH (10 mL) and H2O (3.5 mL) was heated to 85° C. After 24 h the reaction mixture was cooled to ambient temperature. The precipitate was collected by vacuum filtration, washed with minimal MeOH and then water, and dried in the vacuum oven at 50° C. for 4 h to provide the title compound (238 mg, 0.553 mmol, 52% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.79 (s, 1H), 8.35 (s, 1H), 7.89 (d, J=7.4 Hz, 1H), 7.52 (t, J=7.5 Hz, 2H), 7.26 (d, J=8.2 Hz, 1H), 7.11 (t, J=7.8 Hz, 1H), 7.06 (s, 1H), 6.95 (d, J=8.5 Hz, 1H), 6.71 (s, 1H), 5.99 (s, 2H), 5.14-5.00 (m, 1H), 2.21 (dd, J=13.3, 6.2 Hz, 1H), 1.82 (dd, J=13.1, 11.6 Hz, 1H), 1.44 (s, 3H), 1.32 (s, 3H); MS (ESI+) m/z 431 (M+H)+; [α]23D +35.7° (c 0.61, CH3OH).

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with minimal MeOH
  3. dry with materialwater, and dried in the vacuum oven at 50° C. for 4 h

Sources & evidence

ORD record
ord-d5a94bb10e3c4ef18a444e8d7cdb8876
Source dataset
uspto-grants-2013_12
Patent number
US08604053B2

Reaction notes

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