Acetone → HCID 86660265, compound

HRID 449761Notes

Reaction equation

HRID 449761 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C@@H:4]([N:19]1[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1.[CH3:33][C:34]([CH3:36])=O.N([O-])=O.[Na+].[N-:41]=[N+:42]=[N-].[Na+].[OH2:45]>Cl>[C:33]([C:14]1[CH:15]=[CH:16][C:11]([C:10]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([N:19]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:25]3[C:20]2=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:3]([OH:2])=[O:32])=[O:18])=[CH:12][CH:13]=1)(=[O:45])[C:34]1[CH:36]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:1][O:2][C:3](=[O:32])[C@@H:4]([N:19]1[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:18])[C:11]1[CH:12]=[CH:13][C:14]([N:17]=[N+:41]=[N-:42])=[CH:15][CH:16]=1

Participants

8

Reactant 5

HCID 180AcetoneHCID 962Water3×HCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 67993117HCID 67993117, compound

Product 2

HCID 58554740HCID 58554740, compoundHCID 86660265HCID 86660265, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(S)-6-(4-Amino-benzoylamino)-2-carbazol-9-yl-hexanoic acid methyl ester 12 (0.220 g, 0.513 mmol) was dissolved in 5% HCl (9.0 mL) and acetone (9.0 mL) at 0° C. in the dark. NaNO2 (0.039 g, 0.564 mmol) in 2.0 mL H2O was added to the reaction mixture, causing a color change to pale yellow. After 30 min of stiffing, NaN3 (0.333 g, 5.13 mmol) in 5.0 mL H2O was added to the reaction mixture at 0° C. causing an immediate color change from yellow to colorless. The reaction mixture was further stirred for additional 15 min, poured into water (10 mL), and extracted with ethyl acetate (30 mL×2). The combined organic extract was washed with water (10 mL×2) and brine (10 mL×2), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (230-400 mesh), eluting with hexane:acetone (90:10 to 80:20) to furnish a yellow solid (S) 6-(4-azido-benzoylamino)-2-carbazol-9-yl-hexanoic acid methyl ester 13 (0.200 g, 86%).

Workup

  1. customat 0° C.
  2. extractionextracted with ethyl acetate (30 mL×2)
  3. extractionThe combined organic extract
  4. washwas washed with water (10 mL×2) and brine (10 mL×2)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified by flash column chromatography on silica gel (230-400 mesh)
  8. washeluting with hexane:acetone (90:10 to 80:20)

Sources & evidence

ORD record
ord-c197861c38ac48fa8392730534275b01
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Reaction notes

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