HCID 58236597, compound → HCID 58236599, compound

HRID 1026821Notes

Reaction equation

HRID 1026821 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[S:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][C:26]=3[O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:43])[CH2:38][C:39]([O:41]C)=[O:40])=[CH:32][C:31]=3[F:44])[CH:21]=2)=[N:18][CH:19]=1)[CH2:9][CH2:10][O:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[S:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][C:26]=3[O:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][C:37](=[O:43])[CH2:38][C:39]([OH:41])=[O:40])=[CH:32][C:31]=3[F:44])[CH:21]=2)=[N:18][CH:19]=1)[CH2:9][CH2:10][O:11][CH3:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 58236597HCID 58236597, compound

Product 1

HCID 58236599HCID 58236599, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 342 (540 mg, 0.864 mmol) in THF (12 ml) and water (6 ml) was added LiOH monohydrate (363 mg, 8.64 mmol). The mixture was stirred 48 h at room temperature and THF was removed under reduced pressure. The aqueous solution was diluted with water (10 ml) and acidified to pH 4 using 1N HCl. The suspension was filtered and the precipitate was dried under high vacuum to afford compound 343 (485 mg, 0.79 mmol, 92% yield) as a beige solid. MS (m/z): 611.5 (M+H).

Workup

  1. customTHF was removed under reduced pressure
  2. additionThe aqueous solution was diluted with water (10 ml)
  3. filtrationThe suspension was filtered
  4. customthe precipitate was dried under high vacuum

Sources & evidence

ORD record
ord-566e836ad7dc499191304ffb1f02dda7
Source dataset
uspto-grants-2014_05
Patent number
US08729268B2

Reaction notes

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