Sodium Hydroxide → HCID 178445686, compound

HRID 1992790Notes

Reaction equation

HRID 1992790 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([C:14]2[N:18]([CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=3)[N:17]=[C:16]([C:30]3[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=3)[CH:15]=2)=[O:13])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([C:14]2[N:18]([CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=3)[N:17]=[C:16]([C:30]3[CH:31]=[C:32]([F:38])[C:33]([F:37])=[C:34]([F:36])[CH:35]=3)[CH:15]=2)=[O:13])[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178497907HCID 178497907, compound

Product 1

HCID 178445686HCID 178445686, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the intermediate from step E (isomer A, 0.3 g, 0.56 mmol) in 10 ml of THF/MeOH was added 5 N NaOH (1 mL). The reaction was stirred at room temperature for 2 hours and concentrated in vacuo. The residue was acidified with 1N HCl (10 ml). The resulting mixture was extracted with ethyl acetate, dried over anhydrous Na2SO4 filtered and concentrated in vacuo. This material was used in the next step without any further purification. 1H NMR (CD3OD, 500 MHz): 8.26 (d, J=2.1 Hz, 1H), 7.96 (d, J=8.3 Hz, 1H), 7.59 (dd, J=6.6, 8.9 Hz, 1H), 7.31 (d, J=8.3 Hz, 1H), 7.17 (s, 1H), 5.83 (s, 2H), 3.7 (m, 1H), 1.95 (d, J=10.1 Hz, 1H), 1.86 (d, J=10.3 Hz, 1H), 1.3 (m, 2H), 1.15 (m, 2H), 1.0 (m, 1H), 0.88 (s, 9H). LC-MS: 4.25 min; (M+H)=514.2.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThis material was used in the next step without any further purification
  7. custom4.25 min

Sources & evidence

ORD record
ord-d6814dc929b841769a4864b53d974716
Source dataset
uspto-grants-2010_01
Patent number
US07649009B2

Reaction notes

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