HCID 67340629, compound → HCID 67339994, compound

HRID 1675808Notes

Reaction equation

HRID 1675808 reaction equation
C(OC([NH:8][CH:9]1[CH:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][CH3:25])[CH:16]=2)[CH2:13][CH2:12][CH:11]([O:26][C:27](=[O:29])[CH3:28])[CH2:10]1)=O)(C)(C)C>Cl.O1CCOCC1>[NH2:8][CH:9]1[CH:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][CH3:25])[CH:16]=2)[CH2:13][CH2:12][CH:11]([O:26][C:27](=[O:29])[CH3:28])[CH2:10]1

Participants

4

Reactant 1

HCID 67340629HCID 67340629, compound2×

Product 1

HCID 67339994HCID 67339994, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

3.0 g (7.36 mmol) of acetic acid (1SR,3RS,4RS)-3-tert-butoxycarbonylamino-4-(3-ethoxy-4-methoxy-phenyl)-cyclohexyl ester (compound C6) are dissolved in 6 ml of 4 M HCl in dioxane and stirred for 30 min. After removal of the solvent the residue is dissolved in dichloromethane and 25 ml of sat. NaHCO3 solution are added carefully. After phase separation, reextraction of the water layer and drying of the combined organic layers (Na2SO4) the solvent is removed to give 2.25 g of the title compound.

Workup

  1. customAfter removal of the solvent the residue
  2. dissolutionis dissolved in dichloromethane
  3. addition25 ml of sat. NaHCO3 solution are added carefully
  4. customAfter phase separation, reextraction of the water layer
  5. dry with materialdrying of the combined organic layers (Na2SO4) the solvent
  6. customis removed

Sources & evidence

ORD record
ord-7a9e65b137504f9fb30224989a4d1be3
Source dataset
uspto-grants-2011_08
Patent number
US08003798B2

Reaction notes

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