Potassium Bicarbonate → HCID 54414544, compound

HRID 847309Notes

Reaction equation

HRID 847309 reaction equation
[CH:1]1([CH2:7][CH:8]2[CH:12]([CH2:13][CH:14]([CH:18]([CH3:20])[CH3:19])[CH2:15][CH2:16][OH:17])[O:11]C(C)(C)[N:9]2C(OC(C)(C)C)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[K+]>Cl.O1CCOCC1>[NH2:9][C@@H:8]([CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C@@H:12]([OH:11])[CH2:13][C@@H:14]([CH:18]([CH3:19])[CH3:20])[CH2:15][CH2:16][OH:17]

Participants

5

Reactant 2

HCID 516893Potassium BicarbonateHCID 19882234HCID 19882234, compound

Product 1

HCID 54414544HCID 54414544, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

1.1 g (2.67 mmol) of t-butyl 4-(cyclohexylmethyl)-5-(4-hydroxy-2-isopropylbutyl)-2,2-dimethyl-3-oxazolidinecarboxylate are dissolved in 1.85N hydrochloric acid in dioxan and stirred at room temperature for 2 hours. Thereafter, the reaction mixture is poured into 2N potassium bicarbonate solution and extracted with ethyl acetate. The crude product obtained after drying and evaporating the organic extracts is chromatographed on silica gel with a 4:1 mixture of methylene chloride and methanol as the eluting agent, whereby there are obtained 268 mg (37%) of (3S,5S,6S)-6-amino-7-cyclohexyl-5-hydroxy-3-isopropyl-1-heptanol as a resin, MS: 272 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe crude product obtained
  3. customafter drying
  4. customevaporating the organic extracts
  5. customis chromatographed on silica gel with a 4:1 mixture of methylene chloride and methanol as the eluting agent, whereby there

Sources & evidence

ORD record
ord-846cdaead13b490ba247f19271bf572e
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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