Hydrogen chloride-ethyl acetate → HCID 59396570, compound

HRID 2383072Notes

Reaction equation

HRID 2383072 reaction equation
C(OC(=O)[N:7]([CH2:16][C:17]([N:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:29](=[O:31])[NH2:30])[CH:25]=2)[CH:20]1[CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:18])[CH2:8][C:9]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C.Cl.CCOC(C)=O>CCOC(C)=O>[CH:32]1([CH:20]2[C:21]3[C:26](=[CH:25][C:24]([C:29]([NH2:30])=[O:31])=[CH:23][CH:22]=3)[CH2:27][CH2:28][N:19]2[C:17](=[O:18])[CH2:16][NH:7][CH2:8][C:9]2([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 70661788HCID 70661788, compound

Product 1

HCID 59396570HCID 59396570, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Tert-butyl[2-(6-carbamoyl-1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl][(1-hydroxycyclohexyl)methyl]carbamate (357 mg) was dissolved in EtOAc (8 mL). 4 M HCl/EtOAc (0.85 mL) was added to the reaction liquid under ice-cooling, followed by stirring at 60° C. for 5 hours. The solvent was evaporated and water was added to the resulting residue, followed by washing with chloroform. Saturated aqueous sodium bicarbonate was added to the aqueous layer which was then adjusted to a pH of around 8, followed by extraction with chloroform. The extract was washed with saturated brine, and then dried over magnesium sulfate to obtain 1-cyclohexyl-2-{N-[(1-hydroxycyclohexyl)methyl]glycyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxamide (116 mg).

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated
  3. additionwater was added to the resulting residue
  4. washby washing with chloroform
  5. additionSaturated aqueous sodium bicarbonate was added to the aqueous layer which
  6. extractionfollowed by extraction with chloroform
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-5e53749416944f8daa67d7d2bd9d5bdd
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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