Hydrochloric Acid → HCID 58554736, compound

HRID 449765Notes

Reaction equation

HRID 449765 reaction equation
[NH2:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([O:8][CH2:9][CH2:10][O:11][C:12](=[O:31])[CH2:13][C@H:14]([N:18]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:15]([OH:17])=[O:16])=[O:7])=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].[N-:39]=[N+:40]=[N-].[Na+]>CC(C)=O.O>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH2:10][O:11][C:12](=[O:31])[CH2:13][C@H:14]([N:18]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]3[C:30]2=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:15]([OH:17])=[O:16])=[O:7])=[CH:32][CH:33]=1)=[N+:39]=[N-:40]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 58554732HCID 58554732, compound

Product 1

HCID 58554736HCID 58554736, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stiffed solution of 19 (0.115 g, 0.260 mmol) in acetone (6 mL) was added 5% HCl (6 mL) at 0° C. and the solution was stiffing for 5 min NaNO2 (0.020 g, 0.28 mmol) in 1 mL water was added dropwise to the above solution causing an immediate color change from colorless to orange. After 20 min of stirring at 0° C., NaN3 (0.034 g, 0.52 mmol) in 1 mL water was added dropwise to the reaction mixture causing an immediate color changed from orange to colorless to pale yellow. The reaction mixture was stiffed for additional 20 min and extracted with ethyl acetate (50 mL), washed with water (20 mL) and brine (20 mL). The final organic layer was dried over anhydrous Na2SO4, filtrated and concentrated under reduced pressure to obtain (S)-4-(2-(4-azidobenzoyloxy)ethoxy)-2-(9H-carbazol-9-yl)-4-oxobutanoic acid 20 (0.117 g, 96%) as an off white solid.

Workup

  1. waitThe reaction mixture was stiffed for additional 20 min
  2. extractionextracted with ethyl acetate (50 mL)
  3. washwashed with water (20 mL) and brine (20 mL)
  4. dry with materialThe final organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltrated
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45c01d7bdd61441b9661e61e42f0076e
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Reaction notes

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