1,2-Dichloroethane → HCID 22644754, compound

HRID 2414596Notes

Reaction equation

HRID 2414596 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][CH:16]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[C:17]([OH:19])=O)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].C([O-])(O)=O.[Na+].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl.[C:47]([O:51][NH2:52])([CH3:50])([CH3:49])[CH3:48]>CN(C=O)C>[C:47]([O:51][NH:52][C:17](=[O:19])[CH:16]([NH:15][S:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:7][CH:8]=1)(=[O:14])=[O:13])[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([CH3:50])([CH3:49])[CH3:48]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 22644879HCID 22644879, compound

Product 1

HCID 22644754HCID 22644754, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 12.18 g (32.48 mmol) of product of ({[4-(2-butynyloxy)phenyl]sulfonyl}amino)(4-hydroxyphenyl)acetic acid in 5 ml of DMF at room temperature was added 165.65 g (1.95 mol) of NaHCO3, 17.4 g (90.9 mmol) of EDC, 10.53 g (77.95 mmol) of HOBT and 61.2 g (487.2 mmol) of O-t-butylhydroxylamine hydrochloride. The reaction was stirred at 50° C. for 6 h, then at room temperature overnight. DMF was removed. The resulting light brown solid was diluted with ethyl acetate/water, extracted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material was washed with 3-5 ml dichloromethane, The product, ′N-(tert-butoxy)-2-({[4-(2-butynyloxy)phenyl]-sulfonyl}amino)-2-(4-hydroxyphenyl)acetamide, (12 g, 83%) was obtained as a light yellow solid. Electrospray Mass Spec 447.4 (M+H)+

Workup

  1. customat room temperature
  2. customovernight
  3. customDMF was removed
  4. additionThe resulting light brown solid was diluted with ethyl acetate/water
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. washThe crude material was washed with 3-5 ml dichloromethane

Sources & evidence

ORD record
ord-a17ce4d3ca1549299aff549f420323c2
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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