Triethylamine → HCID 68817247, compound

HRID 736775Notes

Reaction equation

HRID 736775 reaction equation
[CH2:1]1[CH:5]2[CH:6]([NH2:11])[CH:7]([C:8]([OH:10])=[O:9])[CH:2]1[CH:3]=[CH:4]2.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>O.O1CCOCC1>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:11][CH:6]2[CH:5]3[CH2:1][CH:2]([CH:3]=[CH:4]3)[CH:7]2[C:8]([OH:10])=[O:9])(=[O:28])=[O:27])=[CH:22][CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 224477HCID 224477, compoundHCID 47383854-(Benzyloxy)benzene-1-sulfonyl chloride

Product 1

HCID 68817247HCID 68817247, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 3-exo-aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (4.60 g, 0.03 mol) and 4-benzyloxy-benzenesulfonyl chloride (8.49 g, 0.03 mol) in water-dioxane (30 mL−30 mL) was added triethylamine (8.38 mL, 0.06 mol) at room temperature. The mixture was stirred for 12 h. The solution was concentrated and the residue was dissolved in water (30 mL). The aqueous solution was extracted with ether (50 mL) and the aqueous layer was acidified with 1 N HCI. The white precipitate was collected and dried to give 3-(4-benzyloxy-benzenesulfonylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (98% yield). Mp=201-203° C. (white solid).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was dissolved in water (30 mL)
  3. extractionThe aqueous solution was extracted with ether (50 mL)
  4. customThe white precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-1c6cf919d62b4217a25ce8919f373840
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

Loading…