Sodium Hydroxide → HCID 69001576, compound

HRID 1909813Notes

Reaction equation

HRID 1909813 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:31]=[CH:30][S:29][CH:28]=3)=[CH:23][CH:22]=2)=[CH:16][CH:15]=1.[OH-].[Na+:34]>CO>[Na+:34].[S:29]1[CH:30]=[CH:31][C:27]([C:24]2[CH:23]=[CH:22][C:21]([CH2:20][C:17]3[CH:18]=[CH:19][C:14]([O:13][CH2:12][C@@H:8]4[CH2:9][CH2:10][CH2:11][N:7]4[CH2:6][CH2:5][CH2:4][C:3]([O-:32])=[O:2])=[CH:15][CH:16]=3)=[CH:26][CH:25]=2)=[CH:28]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69002501HCID 69002501, compound

Product 1

HCID 69001576HCID 69001576, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
58 °C

Procedure

To the product from step 1 (128 mg, 0.29 mmol) in methanol (5 mL) was added 1N NaOH (0.30 mL). The resulting solution was stirred at 58° C. for 5.5 h. The reaction mixture was concentrated in vacuo. The subsequent powder was washed with ether to afford the title compound (85 mg, 68%); LCMS; m/z: 436.9 (M+1); 1H NMR (400 MHz, DMSO-d6); δ 1.54-1.68 (m, 5H), 1.82-1.90 (m, 3H), 2.15-2.26 (m, 2H), 2.70-2.74 (m, 2H), 3.00-3.02 (m, 1H), 3.63-3.67 (m, 1H), 3.87-3.90 (m, 3H), 6.84 (d, J=8.8 Hz, 2H), 7.13 (d, J=8.8 Hz, 2H), 7.22 (d, J=8.0 Hz, 2H), 7.51 (dd, J1=5.2 Hz, J2=1.2 Hz, 1H), 7.60-7.62 (m, 3H), 7.78-7.79 (m, 1H):

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washThe subsequent powder was washed with ether

Sources & evidence

ORD record
ord-d4e4afd3ce47450eb65137688675da33
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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