Hydrochloric Acid → HCID 178493279, compound

HRID 630403Notes

Reaction equation

HRID 630403 reaction equation
[OH:1][C:2]([C:43]1[S:44][CH:45]=[CH:46][CH:47]=1)([C:38]1[S:39][CH:40]=[CH:41][CH:42]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH2:14][CH2:15][O:16][C:17]([NH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([CH2:28][O:29][Si](C(C)(C)C)(C)C)=[CH:22][C:21]=2[Cl:37])=[O:18])[CH3:13])[CH2:8][CH2:7]1)=[O:4].Cl.C(=O)([O-])O.[Na+]>C1COCC1>[OH:1][C:2]([C:38]1[S:39][CH:40]=[CH:41][CH:42]=1)([C:43]1[S:44][CH:45]=[CH:46][CH:47]=1)[C:3]([O:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([N:12]([CH2:14][CH2:15][O:16][C:17]([NH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([CH2:28][OH:29])=[CH:22][C:21]=2[Cl:37])=[O:18])[CH3:13])[CH2:10][CH2:11]1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178493280HCID 178493280, compound2×

Product 1

HCID 178493279HCID 178493279, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-4-[{2-[({[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyphenyl]amino}carbonyl)oxy]ethyl}(methyl)amino]cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 61; 315 mg; 0.44 mmol) in 6 ml THF were added 1.31 ml (1.31 mmol) of aqueous 1M HCl and the system was stirred at room temperature for 2.5 hrs. The solution was basified with aqueous 4% sodium hydrogen carbonate solution and extracted thrice with ethyl acetate. The organic extracts were washed with brine, dried and concentrated. The residue was purified by preparative reversed-phase HPLC (CH2Cl2/isopropanol 10:0 to 9:1) to give 78% of the title compound.

Workup

  1. extractionextracted thrice with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative reversed-phase HPLC (CH2Cl2/isopropanol 10:0 to 9:1)

Sources & evidence

ORD record
ord-ffde776e00c24531ab02fdf4e3a86ffa
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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