Hydrochloric Acid → HCID 58554739, compound

HRID 449769Notes

Reaction equation

HRID 449769 reaction equation
[NH2:1][C:2]1[CH:34]=[CH:33][C:5]([C:6]([O:8][CH2:9][CH2:10][O:11][C:12](=[O:32])[CH2:13][CH2:14][C@H:15]([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:16]([OH:18])=[O:17])=[O:7])=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].[N-:40]=[N+:41]=[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:32])[CH2:13][CH2:14][C@H:15]([N:19]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[C:26]3[C:31]2=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:16]([OH:18])=[O:17])=[O:7])=[CH:33][CH:34]=1)=[N+:40]=[N-:41]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 58554766HCID 58554766, compound

Product 1

HCID 58554739HCID 58554739, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 25 (0.38 g, 0.83 mmol) in acetone (8 mL) was added 5% HCl (8 mL) at 0° C. and the solution was stiffed for 5 min NaNO2 (0.70 g, 1.0 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 stiffing at 0° C., NaN3 (0.107 g, 1.65 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 30 min and extracted with ethyl acetate (100 mL), washed with water (30 mL) and brine (30 mL). The final organic layer was dried over anhydrous Na2SO4, filtrated and concentrated under reduced pressure to obtain (S)-5-(2-(4-azidobenzoyloxy)ethoxy)-2-(9H-carbazol-9-yl)-5-oxopentanoic acid 26 (0.34 g, 85%) as an off white gummy solid.

Workup

  1. waitAfter 20 min of stiffing at 0° C.
  2. waitThe reaction mixture was stiffed for additional 30 min
  3. extractionextracted with ethyl acetate (100 mL)
  4. washwashed with water (30 mL) and brine (30 mL)
  5. dry with materialThe final organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12c117507db84b2a9459922b48812dd6
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Reaction notes

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