Ethanol → HCID 59161323, compound

HRID 545567Notes

Reaction equation

HRID 545567 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][N:6]1[C:18]2[CH:17]=[CH:16][C:15](C(O)=O)=[CH:14][C:13]=2[C:12]2[CH2:11][CH:10]([NH:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[CH2:9][CH2:8][C:7]1=2.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1.C([N:50]([CH2:53]C)CC)C.[CH2:55]([OH:57])[CH3:56]>C1C=CC=CC=1>[CH2:55]([O:57][C:53](=[O:38])[NH:50][C:15]1[CH:16]=[CH:17][C:18]2[N:6]([CH2:5][C:4]3[CH:28]=[CH:29][CH:30]=[C:2]([F:1])[CH:3]=3)[C:7]3[CH2:8][CH2:9][C@@H:10]([NH:22][C:23](=[O:27])[CH:24]([CH3:25])[CH3:26])[CH2:11][C:12]=3[C:13]=2[CH:14]=1)[CH3:56]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 72234597HCID 72234597, compound

Product 1

HCID 59161323HCID 59161323, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Combine (R)-N-(9-(3-fluorobenzyl)-6-isobutyrylamino-6,7,8,9-tetrahydro-5H-carbazole-3-carboxylic acid (Example 188) (0.281 g, 0.67 mmol) with diphenylphosphorylazide (1.3 ml, 0.67 mmol), and triethylamine (0.73 mL, 0.67 mmol) in benzene (3 mL) and heat at reflux for 18 h. Add absolute ethanol and heat for 4 h longer. Concentrate in vacuo, and partition the resulting residue between EtOAc and water. Separate and dry the EtOAc layer over sodium sulfate. Filter and concentrate in vacuo. Redissolve the resulting residue in a minimal amount of EtOAc and pass through a pad of silica to afford 0.248 g (83%) of the title compound. mp: 169-171° C.; MS (ES): m/z 452 (M+1), HPLC: Rt=2.2 min (89%).

Workup

  1. temperatureat reflux for 18 h
  2. temperatureheat for 4 h longer
  3. concentrationConcentrate in vacuo
  4. custompartition the resulting residue between EtOAc and water
  5. customSeparate
  6. dry with materialdry the EtOAc layer over sodium sulfate
  7. filtrationFilter
  8. concentrationconcentrate in vacuo
  9. dissolutionRedissolve the resulting residue in a minimal amount of EtOAc and pass through a pad of silica

Sources & evidence

ORD record
ord-eca6f9033e0c484ca70e90aac2003c91
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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