tert-Butanol → 3-Tert-butoxycarbonylamino-beta-carboline

HRID 569028Notes

Reaction equation

HRID 569028 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3](C(O)=O)[N:2]=1.[C:17]([OH:21])([CH3:20])([CH3:19])[CH3:18].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.C([N:41]([CH2:44]C)CC)C>CS(C)=O>[C:17]([O:21][C:44]([NH:41][C:3]1[N:2]=[CH:1][C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3)=[O:29])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 1732629H-Pyrido(3,4-b)indole-3-carboxylic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 133151183-Tert-butoxycarbonylamino-beta-carboline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.25 g of β-carboline-3-carboxylic acid are dissolved in 4 ml of dimethylsulfoxide while being heated. 10 ml of tert-butanol, 0.25 ml of diphenylphosphoryl azide and 0.17 ml of triethylamine are added to the solution. The reaction mixture is refluxed for 15 minutes. The crystals precipitated during cooling are filtered off, the tert-butanol is evaporated from the filtrate under vacuum and the residue is mixed with 10 ml of water. 0.025 g of 3-tert-butoxycarbonylamino-β-carboline with a 185°-190° C. melting point (methanol) is obtained from the resulting precipitate by chromatography on silica gel (methylene chloride with 5% methanol).

Workup

  1. temperaturewhile being heated
  2. temperatureThe reaction mixture is refluxed for 15 minutes
  3. customThe crystals precipitated
  4. temperatureduring cooling
  5. filtrationare filtered off
  6. customthe tert-butanol is evaporated from the filtrate under vacuum
  7. additionthe residue is mixed with 10 ml of water
  8. customwith a 185°-190° C.
  9. customis obtained from the resulting precipitate by chromatography on silica gel (methylene chloride with 5% methanol)

Sources & evidence

ORD record
ord-23261a56e2c54e7c838328eb763a8261
Source dataset
uspto-grants-1988_03
Patent number
US04731358

Reaction notes

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