Tetrahydrofuran → HCID 68292083, compound

HRID 529440Notes

Reaction equation

HRID 529440 reaction equation
[C:1]123[CH2:14][S:11](=[O:13])(=[O:12])[NH:10][C@H:2]1[CH2:3][CH:4]([C:7]2([CH3:9])[CH3:8])[CH2:5][CH2:6]3.[Li][CH2:16][CH2:17][CH2:18][CH3:19].[C:20](Cl)(=[O:28])[CH2:21]/[CH:22]=[CH:23]/[CH2:24][C:25](Cl)=[O:26].C(=O)=O.[CH3:33][C:34]([CH3:36])=O.[CH2:37]1[CH2:41]OC[CH2:38]1>>[CH3:33][C:34]1([CH3:36])[CH:38]2[CH2:37][CH2:41][C:17]31[C@H:18]([CH2:19]2)[N:10]([C:20](=[O:28])[CH2:21]/[CH:22]=[CH:23]/[CH2:24][C:25]([N:10]1[C@H:2]2[CH2:3][CH:4]4[C:7]([CH3:9])([CH3:8])[C:1]2([CH2:6][CH2:5]4)[CH2:14][S:11]1(=[O:13])=[O:12])=[O:26])[S:11](=[O:13])(=[O:12])[CH2:16]3

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 11116663HCID 11116663, compoundHCID 18522661Acetone cardiceHCID 22870408HCID 22870408, compoundHCID 178418339Butyllithium

Product 1

HCID 68292083HCID 68292083, compoundYield 17.2%

Conditions

Temperature
-78 °C

Procedure

To a round bottom flask was added (2S)-(+)-bornane-10,2-sultam (6.24 gm, 29.0 mmol) and THF (40 mL). The resulting solution was cooled to −78° C. and then n-BuLi (1.6 M in hexanes, 18.6 mL, 29.7 mmol) was added dropwise. The reaction was stirred at −78° C. for 1 hr. Then a solution of (E)-hex-3-enedioyl dichloride in THF (2 mL) was slowly added. After 30 min the dry ice/acetone bath was replaced by an ice bath and the reaction was stirred at 0° C. for 1 hr. After this time, the reaction was quenched by addition of saturated aqueous NH4Cl. The mixture was partitioned between EtOAc and water. The organic phase was isolated, dried over MgSO4, filtered and concentrated. The crude product was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give (3E)-1,6-bis((7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3a,6-methano-2,1-benzothiazol-1(3H,4H)-yl)hex-3-ene-1,6-dione (1.28 gm, 2.38 mmol, 17.2% yield) as a white solid. Anal. Calcd. for C26H38N2O6S2 m/z 538.2. found: 539.1 (M+H)+.

Workup

  1. stirringthe reaction was stirred at 0° C. for 1 hr
  2. customAfter this time, the reaction was quenched by addition of saturated aqueous NH4Cl
  3. customThe mixture was partitioned between EtOAc and water
  4. customThe organic phase was isolated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified
  9. washeluting with a gradient of 0-100% EtOAc/Hex

Sources & evidence

ORD record
ord-2d8a9dd7fb0048b0b28894c8f69c30b4
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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