Hydrochloric Acid → HCID 18365425, compound

HRID 380584Notes

Reaction equation

HRID 380584 reaction equation
[NH2:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][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.Cl>O1CCOCC1.O>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([NH:1][C:2]2([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]2)(=[O:27])=[O:26])=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2901CycloleucineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 18365425HCID 18365425, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-aminocyclopentane-1-carboxylic acid (6.0 grams, 46.5 mmole) and triethylamine (14 mL, 100 mmole) in dioxane (90 mL) and water (90 mL) was added 4methoxybenzenesulfonyl chloride (10.6 grams, 51.3 mmole). The resulting mixture was stirred at room temperature for 4 hours, acidified with aqueous 1N hydrochloric acid solution, and extracted twice with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over magnesium sulfate and concentrated to leave a tan solid which was triturated with chloroform to afford 1-(4-methoxybenzenesulfonylamino)-cyclopentane-1 carboxylic acid as a white solid, 5.42 grams (39%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined ethyl acetate extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto leave a tan solid which
  6. customwas triturated with chloroform

Sources & evidence

ORD record
ord-e9e303f692b74632b89370560ae03b1e
Source dataset
uspto-grants-2001_10
Patent number
US06303636B1

Reaction notes

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