Dichloromethane → HCID 86650114, compound

HRID 2179747Notes

Reaction equation

HRID 2179747 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][C@H:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:4]1.C(Cl)Cl.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C([O-])(O)=O.[Na+]>>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:1][CH2:2][C@@H:3]2[CH2:7][C@H:6]([NH:8][C:9]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:15])[CH:5]=[CH:4]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 18453470HCID 18453470, compound

Product 1

HCID 86650114HCID 86650114, compoundYield 70.9%

Conditions

Temperature
0 °C

Procedure

To a stirred solution of tert-butyl (1S,4R)-4-(hydroxymethyl)cyclopent-2-enylcarbamate (Intermediate 6-step 2, about 4.5 g, 21.12 mmol) in DCM (50 ml) triethyl amine (about 9.5 ml, 68.1 mmol) was added at room temperature and cooled to about 0° C. After ten minutes, 4-methylbenzene-1-sulfonyl chloride (about 6.0 g) was added and stirred the reaction at room temperature for about 6 hours and completion of the reaction was monitored by TLC. Reaction mixture was neutralized with saturated NaHCO3 and extracted with DCM, the organic layer was dried over Na2SO4 and concentrated under reduced pressure to furnish the title compound (5.5 g) as a light yellow liquid. 1H NMR (300 MHz, CDCl3): 1.45 (s, 9H); 246-2.55 (m, 4H); 2.90-2.91 (m, 1H); 3.95-3.98 (m, 2H); 4.59-4.70 (m, 2H); 5.66-5.77 (m, 2H); 7.34-7.37 (d, J=9 Hz, 2H); 7.77-7.80 (d, J=9 Hz, 2H).

Workup

  1. waitAfter ten minutes
  2. customthe reaction at room temperature for about 6 hours
  3. customReaction mixture
  4. extractionextracted with DCM
  5. dry with materialthe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c9b222fc38be44aa8cc75678d68407dc
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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