Acetic Acid → HCID 22006220, compound

HRID 323580Notes

Reaction equation

HRID 323580 reaction equation
[CH:1]1([C:4]2[C:5]3[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=3[N:7]([CH2:11][CH3:12])[CH:8]=[CH:9][N:10]=2)[CH2:3][CH2:2]1.CC(C)([O-])C.[K+].C(C1C=C(C(C)C)C=C(C(C)C)C=1S([N:41]=[N+:42]=[N-:43])(=O)=O)(C)C.C(O)(=O)C>C1COCC1>[N:41]([C:9]1[N:10]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[C:5]2[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=2[N:7]([CH2:11][CH3:12])[CH:8]=1)=[N+:42]=[N-:43]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 22006219HCID 22006219, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22006220HCID 22006220, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
30 °C

Procedure

To a stirring solution of 5-cyclopropyl-1-ethyl-1H-benzo[e][1,4]diazepine (6.4 g, 0.028 mol) in THF (125 ml) cooled to −78° C. was added potassium tert-butoxide (2.05 eq, 0.057 mol, 57.2 ml of a 1 M solution in THF) dropwise over 15 min. A solution of 2,4,6-triisopropylphenyl-sulfonylazide (9.5 g, 0.031 mol) in THF (100 ml) was added over 5 min. The solution was stirred for 10 min, acetic acid (7.7 ml,0.123 mol) was added and the reaction warmed to 30° C. for 2 hour. The reaction was concentrated the residue dissolved in dichloromethane (200 mL) and washed with satd. NaHCO3 (200 ml). The aqueous layer was back extracted with dichloromethane (100 ml). The organic layers were combined, dried with Na2SO4 and evaporated to a foam. The foam was chromatographed over silica eluting with 30% ethyl acetate:hexane. The appropriate fractions were collected and evaporated under reduced pressure to give 5.83 g of a powder. MP=158-160° C.

Workup

  1. concentrationThe reaction was concentrated the residue
  2. dissolutiondissolved in dichloromethane (200 mL)
  3. washwashed with satd
  4. extractionThe aqueous layer was back extracted with dichloromethane (100 ml)
  5. dry with materialdried with Na2SO4
  6. customevaporated to a foam
  7. customThe foam was chromatographed over silica eluting with 30% ethyl acetate
  8. customThe appropriate fractions were collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c68393465a474d5ca0288ed7eec303ee
Source dataset
uspto-grants-2001_04
Patent number
US06214823B1

Reaction notes

Loading…