Dicyclohexylcarbodiimide → HCID 86755466, compound

HRID 1421521Notes

Reaction equation

HRID 1421521 reaction equation
[CH2:1]([O:8][NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:11][O:12][C:13]12[O:19][C:16]([S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])([CH:17]=[CH:18]1)[CH:15]([C:29](O)=[O:30])[CH2:14]2.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([O:8][NH:9][C:29]([CH:15]1[CH2:14][C:13]2([O:12][CH3:11])[O:19][C:16]1([S:20]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:21])=[O:22])[CH2:17][CH2:18]2)=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 102312Benzyloxyamine hydrochlorideHCID 86755467HCID 86755467, compound

Product 1

HCID 86755466HCID 86755466, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Added the O-benzylhydroxylamine·hydrochloric acid (0.387 grams, 2.43 mmol) to a stirred solution of 3-(4-methoxy-phenylsulfonyl-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid in methylene chloride (5 ml). Added 4-dimethylaminopyridine (0.306 grams, 2.51 mmol) and stirred approximately one-half hour (until solids dissolved), then added the 1,3-dicyclohexylcarbodiimide (0.250 grams, 1.21 mmol) and stirred at room temperature overnight. The reaction was filtered through a pad of Celite and the filtrate concentrated in vacuo to give 1.06 grams of 3-(4-Methoxyphenylsulfonyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid benzyloxyamide. Took this up in methanol and decanted filtrate from fine needle crystals. Concentration of filtrate gave 0.82 grams of 3-(4-Methoxyphenylsulfonyl-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid benzyloxyamide.

Workup

  1. dissolution(until solids dissolved)
  2. filtrationThe reaction was filtered through a pad of Celite
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-c372faec54fc4c0598143dde2540f8a3
Source dataset
uspto-grants-2000_06
Patent number
US06077864

Reaction notes

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