Dimethyl Sulfoxide → HCID 86595788, compound

HRID 1241448Notes

Reaction equation

HRID 1241448 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([C@@H:20]([CH2:27][C:28]3[N:29]=[C:30]([CH2:33][CH2:34][CH2:35][CH2:36][OH:37])[S:31][CH:32]=3)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:19][C:14]=2[O:13][CH2:12]1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([C@@H:20]([CH2:27][C:28]3[N:29]=[C:30]([CH2:33][CH2:34][CH2:35][CH:36]=[O:37])[S:31][CH:32]=3)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:19][C:14]=2[O:13][CH2:12]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86595787HCID 86595787, compound

Product 1

HCID 86595788HCID 86595788, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

Dimethyl sulfoxide (1.47 mL, 3.15 mmol) was cooled in 5 mL CH2Cl2 to −70° C. for 10 min. The oxalyl chloride (2.0M in CH2Cl2, 4.9 mL, 9.85 mmol) was added, and the reaction was allowed to stir at −70° C. for 1 hr. A solution of (3S)-Ethyl 3-(1,3-benzodioxol-5-yl)-4-[2-(4-hydroxybutyl)-1,3-thiazol-4-yl]butanoate (2.57 g, 6.56 mmol) in CH2Cl2 (5 mL) was added to the reaction and stirred at −70° C. for 1 hr. Add triethylamine (5.96 mL, 6.52 mmol) and allow to warm to room temperature. Dilute with ethyl acetate, wash with water, 1 N HCl, water, and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo and purified via silica gel chromatography (eluent: 3:1 Hexane:Ethyl Acetate) to give the product as a colorless oil. Yield: 1.95g (76%) 1H NMR (DMSO-d6) δ9.68–9.65 (m, 1H), 6.98–6.95 (m, 1H), 6.75–6.71 (m, 1H), 6.63–6.58 (m, 1H), 5.94 (s, 2H), 3.96–3.88 (q, 2H), 3.47–3.38 (m, 1H), 3.00–2.85 (m, 4H), 2.68–2.48 (m, 4H), 1.97–1.88 (m, 2H), 1.08–1.01 (t, 3H).

Workup

  1. stirringstirred at −70° C. for 1 hr
  2. temperatureto warm to room temperature
  3. washwash with water, 1 N HCl, water, and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified via silica gel chromatography (eluent: 3:1 Hexane:Ethyl Acetate)

Sources & evidence

ORD record
ord-b8c6e26325904f108634be5eec753330
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

Loading…