Hydrochloric Acid → HCID 76774658, compound

HRID 446838Notes

Reaction equation

HRID 446838 reaction equation
C([O:3][C:4]([CH:6]1[NH:30][CH2:29][C@:28]2([C:31](=[O:34])[CH2:32][OH:33])[C@H:7]1[CH2:8][C@H:9]1[C@H:22]3[C@@:13]([F:26])([C@:14]4([CH3:25])[C:19]([C@@H:20]([F:23])[CH2:21]3)=[CH:18][C:17](=[O:24])[CH:16]=[CH:15]4)[C@@H:12]([OH:27])[CH2:11][C@@:10]12[CH3:35])=[O:5])C.Cl>C1COCC1.O.[Cl-].[Na+].O>[CH2:8]([N:30]1[CH2:29][C:28]2([C:31](=[O:34])[CH2:32][OH:33])[CH:7]([CH2:8][CH:9]3[CH:22]4[C:13]([F:26])([C:14]5([CH3:25])[C:19]([CH:20]([F:23])[CH2:21]4)=[CH:18][C:17](=[O:24])[CH:16]=[CH:15]5)[CH:12]([OH:27])[CH2:11][C:10]32[CH3:35])[CH:6]1[C:4]([OH:3])=[O:5])[C:9]1[CH:22]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 58392737HCID 58392737, compound

Product 1

HCID 76774658HCID 76774658, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of compound 119 (66 mg; 0.113 mmol) in dry THF (3 ml) and water (1 ml) 1 N NaOH (400 μl) is added and the reaction mixture is stirred at RT overnight. The reaction mixture is poured into 1 N HCl (10 ml) and brine (10 ml), and the aqueous phase is extracted with AcOEt (3×40 ml). The combined organic extracts are dried and concentrated. Crude is purified by preparative HPLC, to afford title compound (15% yield).

Workup

  1. extractionthe aqueous phase is extracted with AcOEt (3×40 ml)
  2. customThe combined organic extracts are dried
  3. concentrationconcentrated
  4. customCrude is purified by preparative HPLC

Sources & evidence

ORD record
ord-a84a5cf4c8cd442e989813e4a8e3a482
Source dataset
uspto-grants-2013_07
Patent number
US08481517B2

Reaction notes

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