Hydrochloric Acid → HCID 178484861, compound

HRID 630376Notes

Reaction equation

HRID 630376 reaction equation
[OH:1][C:2]([C:26]1[S:27][CH:28]=[CH:29][CH:30]=1)([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)[C:3]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12](C(OC(C)(C)C)=O)[CH3:13])[CH2:8][CH2:7]1)=[O:4].Cl>O1CCOCC1>[OH:1][C:2]([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[S:27][CH:28]=[CH:29][CH:30]=1)[C:3]([O:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([NH:12][CH3:13])[CH2:10][CH2:11]1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178486063HCID 178486063, compound2×

Product 1

HCID 178484861HCID 178484861, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of trans-4-[(tert-butoxycarbonyl)(methyl)amino]cyclohexyl hydroxy(di-2-thienyl)acetate (intermediate 4; 8.1 g, 0.01 mol) in dioxane (13.5 mL) was added hydrogen chloride 4M in dioxane (27 mL). The mixture was stirred at room temperature for 24 hours. The precipitate obtained was filtrated and washed with ether. The crude was dissolved in water and potassium carbonate was added until pH=8-9. The product was extracted with ethyl acetate and the organic layer was washed with brine, dried and evaporated to dryness giving the title compound as a white solid (78%).

Workup

  1. customThe precipitate obtained
  2. filtrationwas filtrated
  3. washwashed with ether
  4. dissolutionThe crude was dissolved in water
  5. additionpotassium carbonate was added until pH=8-9
  6. extractionThe product was extracted with ethyl acetate
  7. washthe organic layer was washed with brine
  8. customdried
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-2d8c6416cbac4bb49c7ede0042cd467f
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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