Hydrochloric Acid → HCID 70088087, compound

HRID 847316Notes

Reaction equation

HRID 847316 reaction equation
[CH2:1]([NH:5][C:6](/[CH:8]=[CH:9]/[C@H:10]([CH:33]([CH3:35])[CH3:34])[CH2:11][C@@H:12]1[O:16]C(C)(C)[N:14](C(OC(C)(C)C)=O)[C@H:13]1[CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:7])[CH2:2][CH2:3][CH3:4].Cl>CO>[NH2:14][C@@H:13]([CH2:26][CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1)[C@@H:12]([OH:16])[CH2:11][C@@H:10]([CH:33]([CH3:34])[CH3:35])/[CH:9]=[CH:8]/[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86746082HCID 86746082, compound

Product 1

HCID 70088087HCID 70088087, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.53 g (1.07 mmol) of t-butyl (4S,5S)-5-[(S,E)-4-(butylcarbamoyl)-2-isopropyl-3-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate is dissolved in 18.2 ml of methanol and treated at 10° with 6.4 ml of 3.88M hydrochloric acid in methanol. The reaction mixture is subsequently stirred at room temperature for 5 hours and thereafter evaporated. The residue is dissolved in methylene chloride and the methylene chloride solution is washed with 2N sodium bicarbonate solution, dried over potassium carbonate and evaporated under reduced pressure. In this manner there is obtained 0.314 g of (E,4S,6S,7S)-7-amino-N-butyl-8-cyclohexyl-6-hydroxy-4-isopropyl-2-octenamide as an oil which is used in the next step without further purification.

Workup

  1. customevaporated
  2. dissolutionThe residue is dissolved in methylene chloride
  3. washthe methylene chloride solution is washed with 2N sodium bicarbonate solution
  4. dry with materialdried over potassium carbonate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3efa01ae3e75416497664659f807f5c0
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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