HCID 4447312, compound → HCID 22842919, compound

HRID 1078090Notes

Reaction equation

HRID 1078090 reaction equation
C([Li])CCC.[CH2:6]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:7][CH2:8][CH3:9].[CH:15]1([CH2:21][C@H:22]2[C@H:26]([C:27](=[O:32])[CH2:28][CH2:29][CH2:30][CH3:31])[O:25][C:24]([CH3:34])([CH3:33])[N:23]2[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C1(CC2COC(C)(C)N2C(OC(C)(C)C)=O)CCCCC1>O1CCCC1.CO>[CH2:6]([NH:10][S:11]([CH2:14][C:27]([C@@H:26]1[O:25][C:24]([CH3:34])([CH3:33])[N:23]([C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])[C@H:22]1[CH2:21][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([CH2:28][CH2:29][CH2:30][CH3:31])[OH:32])(=[O:13])=[O:12])[CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 4447312HCID 4447312, compoundHCID 21624152HCID 21624152, compoundHCID 57170354HCID 57170354, compoundHCID 178418339Butyllithium

Product 1

HCID 22842919HCID 22842919, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (4.48 ml., 11.2 mmole, 2.8 eq., 2.5M in hexane) was added to a solution of N-butylmethanesulfonamide [846 mg., 5.6 mmole, 1.4 eq., prepared as described in Example 1(a)] in tetrahydrofuran (16 ml., 0.35M) at -40° and stirred for 10 minutes. The reaction was then warmed to 0°, stirred for 30 minutes and cooled to -40°. (4S-trans)-4-(Cyclohexylmethyl)-2,2-dimethyl-5-(1-oxopentyl)-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester (1.5 g., 3.93 mmole, 1 eq.) in tetrahydrofuran (4 ml., 1.0M) was then added. After 90 minutes at -40°, the reaction was quenched with aqueous saturated NH4Cl, warmed to room temperature and extracted three times with ether. The organic extracts were dried (Na2SO4), filtered through MgSO4, and concentrated. The residue was chromatographed on silica gel (Merck, 80 g.) eluting with hexane:acetone (10:1) to provide 237 mg. of (4S-trans)-5-[2-[butylamino)sulfonyl]-1-butyl-1-hydroxyethyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester, isomer A; [α]D =+4.2° (c=1.0, methanol) and 101 mg. of isomer B; m.p. 138°-140°; [α]D =+5.5° (c=1.0, methanol) and 1.518 g. of a mixture of isomer A and isomer B.

Workup

  1. temperatureThe reaction was then warmed to 0°
  2. stirringstirred for 30 minutes
  3. temperaturecooled to -40°
  4. waitAfter 90 minutes at -40°
  5. customthe reaction was quenched with aqueous saturated NH4Cl
  6. extractionextracted three times with ether
  7. dry with materialThe organic extracts were dried (Na2SO4)
  8. filtrationfiltered through MgSO4
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel (Merck, 80 g.)
  11. washeluting with hexane:acetone (10:1)
  12. customto provide 237 mg
  13. additionof a mixture of isomer A and isomer B

Sources & evidence

ORD record
ord-54a27fd2486e46c89ad624972cba7963
Source dataset
uspto-grants-1996_08
Patent number
US05545838

Reaction notes

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