Tetrahydrofuran → HCID 10612452, compound

HRID 1611240Notes

Reaction equation

HRID 1611240 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[CH3:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C1C[O:28]CC1>>[C:19]([N:9]1[C@@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])(=[O:28])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8058HexaneHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 10612452HCID 10612452, compound

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-(S)-benzyloxazolidin-2-one (56 mmol) (Aldrich, Milwaukee, Wis.) in THF at −78° C. is added 2.5 M n-BuLi in hexane (22.4 mL, 56 mmol) and the reaction is stirred at −78° C. for 2 hours. To this is added via cannula a −78° C. solution of acid chloride A-1 (R=hexanoyl, 65 mmol) in THF and the mixture is stirred at −78° C. for 2 hours, then allowed to warm to rt and stirred overnight. The reaction is then quenched with aqueous saturated NH4Cl, extracted with EtOAc, dried and purified by silica gel chromatography (hexanes/EtOAc) to afford N-hexanoyl-4-(S)-benzyloxazolidin-2-one (A-2).

Workup

  1. stirringthe mixture is stirred at −78° C. for 2 hours
  2. temperatureto warm to rt
  3. stirringstirred overnight
  4. customThe reaction is then quenched with aqueous saturated NH4Cl
  5. extractionextracted with EtOAc
  6. customdried
  7. custompurified by silica gel chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-04bb36b89b4148f2a23f53c38059f863
Source dataset
uspto-grants-2006_01
Patent number
US06987104B2

Reaction notes

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