Lithium Hydroxide → HCID 70869147, compound

HRID 1844729Notes

Reaction equation

HRID 1844729 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([C:19]2[N:20]([CH2:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:21]([CH3:28])=[C:22]([S:24](=[O:27])(=[O:26])[NH2:25])[CH:23]=2)[CH:18]=1)[O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>CO.C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([C:19]2[N:20]([CH2:29][CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)[C:21]([CH3:28])=[C:22]([S:24](=[O:26])(=[O:27])[NH2:25])[CH:23]=2)[CH:18]=1)[O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 70869231HCID 70869231, compound

Product 1

HCID 70869147HCID 70869147, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 15 (126 mg, 0.25 mmol) in methanol and THF (30 mL; 1:1) was added LiOH (25 mg, 1 mmol) and the mixture was stirred at rt overnight. The residue was concentrated and then poured into water and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, evaporated and purified by CC to give compound 16 (98 mg, 80%). 1H-NMR (400 MHz, DMSO-d6) δ: 12.2 (br s, 1H), 6.91-6.89 (m, 4H), 6.68 (s, 1H), 6.29 (s, 1H), 4.02-3.98 (m, 2H), 3.81-3.79 (m, 2H), 2.43 (s, 3H) 2.40-2.36 (m, 5H), 1.94-1.91 (m, 2H), 1.48-1.46 (m, 3H), 1.27-1.24 (m, 12H), 0.96-0.94 (m, 3H), 0.66-0.64 (m, 2H). MS Found: 491 (M+1).

Workup

  1. concentrationThe residue was concentrated
  2. additionpoured into water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by CC

Sources & evidence

ORD record
ord-d83334fb78f94481a6be3dd84300fc76
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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