4-Methoxybenzenesulfonyl chloride → AC1M6VJW

HRID 1954081Notes

Reaction equation

HRID 1954081 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.C(N(CC)CC)C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>O.O1CCOCC1.CN(C)C1C=CN=CC=1>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([N:5]2[CH2:6][C@H:2]([OH:1])[CH2:3][C@@H:4]2[C:7]([OH:9])=[O:8])(=[O:27])=[O:26])=[CH:23][CH:24]=1

Participants

7

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 440014Cis-4-Hydroxy-D-Proline

Product 1

HCID 2430970AC1M6VJW

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Cis-4-hydroxy-D-proline (9.0 g, 68.6 mmol) is dissolved in 100 mL mixture of water and p-dioxane (1:1) and then triethyl amine (19.1 mL, 137.3 mmol), 4-methoxyphenylsulfonyl chloride (15.6 g, 75.5 mmol), and 4-dimethylaminopyridine (0.86 g, 6.86 mmol) are added. The solution is stirred at room temperature overnight. The reaction mixture is washed with sodium bicarbonate and extracted once with ether. The water layer is acidified with 1N HCl until pH~2 is achieved and then the solution is extracted three times with ethyl acetate. The ethyl acetate layers are washed with ammonium chloride, and dried (MsSO4), filtered and evaporated to give the crude acid. Cl+ MS: m/z (rel intensity) 302.0(M+ +H, 100).

Workup

  1. washThe reaction mixture is washed with sodium bicarbonate
  2. extractionextracted once with ether
  3. extractionthe solution is extracted three times with ethyl acetate
  4. washThe ethyl acetate layers are washed with ammonium chloride
  5. customdried (MsSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-dff8e3f6663d4834ba0a5bd35f6ac0f1
Source dataset
uspto-grants-2000_09
Patent number
US06121272

Reaction notes

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