HCID 67340629, compound → HCID 67339994, compound

HRID 2190272Notes

Reaction equation

HRID 2190272 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-methoxyphenyl)-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-4d1883a53f1447cabcdcace8da07e904
Source dataset
uspto-grants-2012_12
Patent number
US08324391B2

Reaction notes

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