Hydrochloric Acid → 5-[2-[(Butylamino)carbonyl]-3-methyl-1-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester

HRID 1941348Notes

Reaction equation

HRID 1941348 reaction equation
C[Al](C)C.[CH2:5]([NH2:9])[CH2:6][CH2:7][CH3:8].C([O:12][C:13]([C:15]([CH:38]([CH3:40])[CH3:39])=[CH:16][CH:17]1[O:21][C:20]([CH3:23])([CH3:22])[N:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:18]1[CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=O)C.Cl>CCCCCC.C(Cl)(Cl)Cl.ClCCCl>[CH2:5]([NH:9][C:13]([C:15]([CH:38]([CH3:40])[CH3:39])=[CH:16][CH:17]1[O:21][C:20]([CH3:23])([CH3:22])[N:19]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH:18]1[CH2:31][CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1)=[O:12])[CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8007ButylamineHCID 16682925TrimethylaluminumHCID 867517835-[2-[(Ethoxy)carbonyl]-3-methyl-1-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester

Product 1

HCID 867517825-[2-[(Butylamino)carbonyl]-3-methyl-1-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl esterYield 88%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent2×HCID 6212ChloroformSolventHCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

The procedure of Poss, M. A. and Reid, J. A. (Tet. Lett. 1992, 33 (11), 1411-14) was used. A 2.0M solution of trimethylaluminum (1.25 mL, 2.5 mmol) in hexane was added to a 1,2-dichloroethane (1.25 mL) solution containing butylamine (0.25 mL, 2.5 mmol) at r.t. and stirred for one h. A 1,2-dichloroethane (1.25 mL) solution containing 5-[2-[(ethoxy)carbonyl]-3-methyl-1-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester (424 mg, 1.0 mmol) was added to the reactants prepared above and heated at 70° C. for 16 h. The reaction was cooled to 0° C., diluted with CHCl3, and treated with 1N HCl. The organic phase was separated and the aqueous phase extracted with CHCl3 (2×). The combined organic extracts were dried (Na2SO4), filtered through MgSO4 and concentrated in vacuo. Silica gel chromatography (5:1 hexane:Et2O) of the concentrate afforded the title compound (408 mg, 88%). MS (ESI) m/e 463 (M-H)-.

Workup

  1. additionwas added to the reactants
  2. customprepared above and
  3. temperatureThe reaction was cooled to 0° C.
  4. customThe organic phase was separated
  5. extractionthe aqueous phase extracted with CHCl3 (2×)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered through MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-787177fad9ff45a0a5290853c699790c
Source dataset
uspto-grants-1997_12
Patent number
US05703129

Reaction notes

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