Lithium Hydroxide → HCID 178427606, compound

HRID 576547Notes

Reaction equation

HRID 576547 reaction equation
C[O:2][C:3](=[O:57])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:56])[C@@H:17]([NH:42][S:43]([C:46]2[CH:55]=[CH:54][C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[CH:47]=2)(=[O:45])=[O:44])[CH2:18][CH2:19][CH2:20][NH:21]/[C:22](/[NH2:41])=[N:23]/[S:24]([C:27]2[C:28]([CH3:40])=[C:29]([CH3:39])[C:30]3[O:34][C:33]([CH3:36])([CH3:35])[CH2:32][C:31]=3[C:37]=2[CH3:38])(=[O:26])=[O:25])[CH2:12][CH2:11]1)=[O:9].[Li+].[OH-]>C1COCC1.O>[NH2:41]/[C:22](/[NH:21][CH2:20][CH2:19][CH2:18][C@H:17]([NH:42][S:43]([C:46]1[CH:55]=[CH:54][C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:47]=1)(=[O:45])=[O:44])[C:16]([N:13]1[CH2:12][CH2:11][N:10]([C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:57])=[O:2])[CH2:15][CH2:14]1)=[O:56])=[N:23]\[S:24]([C:27]1[C:28]([CH3:40])=[C:29]([CH3:39])[C:30]2[O:34][C:33]([CH3:36])([CH3:35])[CH2:32][C:31]=2[C:37]=1[CH3:38])(=[O:25])=[O:26]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178500350HCID 178500350, compound

Product 1

HCID 178427606HCID 178427606, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound O (2.1 g, 2.08 mmol) in THF (5 mL), H2O (5 mL) was added 2 M aq LiOH (6 mL). The reaction mixture was stirred at room temperature for 2 h. Solvents were removed in vacuo, then the residue was dissolved in water (˜50 mL), acidified with saturated aqueous NaHSO4 (˜100 ml) and extracted with EtOAc (2×100 ml). The organic layer was dried over Na2SO4 and removal of the solvent gave compound P (1.72 g, 2.08 mmol). LC-MS [M+H] 813.5 (C39H52N6O9S2+H, calc: 813.3). Compound P was used without further purification.

Workup

  1. customSolvents were removed in vacuo
  2. dissolutionthe residue was dissolved in water (˜50 mL)
  3. extractionextracted with EtOAc (2×100 ml)
  4. dry with materialThe organic layer was dried over Na2SO4 and removal of the solvent

Sources & evidence

ORD record
ord-c4e9024492b241c7a186179f73d7b0f6
Source dataset
uspto-grants-2015_05
Patent number
US09040032B2

Reaction notes

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