Triethylamine → HCID 87740271, compound

HRID 2057112Notes

Reaction equation

HRID 2057112 reaction equation
[CH3:1][CH:2]([CH3:12])[C@H:3]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[C@H:4](O)[CH3:5].CCN(CC)CC.CS(Cl)(=O)=O.[CH3:25][C:26]([SH:28])=O>C1C=CC=CC=1.O.C(Cl)Cl>[CH3:1][CH:2]([CH3:12])[C@H:3]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[C@H:4]([C:26](=[S:28])[CH3:25])[CH3:5]

Participants

8

Reactant 4

HCID 8471Triethylamine2×HCID 10484Thioacetic acidHCID 31297Methanesulfonyl chlorideHCID 59660039HCID 59660039, compound

Product 1

HCID 87740271HCID 87740271, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a three-necked flask, compound (6b4a) (0.855 g, 5.0 mmol), CH2Cl2 (20 mL) and NEt3 (1.01 g, 10.0 mmol) are added under nitrogen system. Next, MeSO2Cl (0.69 g, 6.0 mmol, dissolved in 20 mL CH2Cl2) is added dropwisely at 0° C. After complete reaction for 2 hours, a coarse product is obtained through repeated depressing concentration and adding benzene therein. The coarse product is then added into benzene (20 mL) with refluxing, and MeCOSH (0.46 g, 6.0 mmol) and NEt3 (1.01 g, 10.0 mmol) dissolved in 20 mL benzene are injected into the above solution under the nitrogen system. After 12 hours, H2O (20 mL) is added to terminate the reaction. The product is repeatedly extracted with EtOAc (20 mL), wherein the organic phase is dehydrated with Na2SO4. A coarse product is obtained after filtration and concentration. Column chromatography (Silica gel 70 g, eluent is n-Hexane:NEt3=100:1) is used to purify the coarse product and two orange liquids, compound (6b4b) (0.229 g) and compound (2f4b) (0.458 g), are obtained. The yields of compound (6b4b) and compound (2f4b) are 20% and 40%, respectively. The other analysis for compound (6b4b) includes:

Workup

  1. customAfter complete reaction for 2 hours
  2. customa coarse product is obtained
  3. concentrationconcentration
  4. additionadding benzene
  5. additionThe coarse product is then added into benzene (20 mL)
  6. temperaturewith refluxing
  7. customto terminate
  8. customthe reaction
  9. extractionThe product is repeatedly extracted with EtOAc (20 mL), wherein the organic phase

Sources & evidence

ORD record
ord-16cd10d66cc74f4ea9f546926143bd71
Source dataset
uspto-grants-2008_02
Patent number
US07335781B2

Reaction notes

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