Hydrochloric Acid → HCID 70869330, compound

HRID 332601Notes

Reaction equation

HRID 332601 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:12])=[CH:8][CH:9]=1)=[O:4].COC(C1SC(C[C@H](C(OC(C)(C)C)=O)C)=CC=1)=O.[OH-].[Li+].Cl>CO.O1CCCC1>[C:16]([O:15][C:13]([C@H:11]([CH3:12])[CH2:10][C:7]1[S:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 70869444HCID 70869444, compoundHCID 70869512HCID 70869512, compound

Product 1

HCID 70869330HCID 70869330, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using 5-(2-tert-butoxycarbonylpropyl)thiophene-2-carboxylic acid methyl ester obtained as an intermediate of Example 13, and in the same manner as in Example 31, optical resolution was performed. The obtained (2R)-5-(2-tert-butoxycarbonylpropyl) thiophene-2-carboxylic acid methyl ester (0.18 g, 0.63 mmol) was suspended in methanol (1.6 mL) and tetrahydrofuran (1.6 mL), 1N aqueous lithium hydroxide solution (1.6 mL) was added, and the mixture was stirred overnight. 1N Hydrochloric acid (2 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (0.17 g).

Workup

  1. customobtained as an intermediate of Example 13
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5189c73ab9b748be9285e314d5de2a80
Source dataset
uspto-grants-2014_11
Patent number
US08877805B2

Reaction notes

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