Tryptamine → HCID 11242389, compound

HRID 1591672Notes

Reaction equation

HRID 1591672 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.[NH2:25][CH2:26][CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1.[C:37]([NH:40][CH2:41][C:42](O)=[O:43])(=[O:39])[CH3:38]>CN(C=O)C>[C:37]([NH:40][CH2:41][C:42]([NH:25][CH2:26][CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)=[O:43])(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 1150TryptamineHCID 8471TriethylamineHCID 10972AcetylglycineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 11242389HCID 11242389, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Diphenylphosphorylazide (5.8 ml, 27.5 ml) and triethylamine (3.85 ml, 27.5 ml) were added in succession to a mixture of tryptamine (4.32 g, 27 mmol) and N-acetylglycine (3.3 g, 28 mmol) in DMF (100 ml) cooled to 0° C. The mixture was stirred under nitrogen at ambient temperature for 12 h, then the solvent was eliminated under reduced pressure. The residue obtained was flash chromatographed on silica gel to produce the expected product (m=5.5 g, 21 mmol), giving a yield of 78%.

Workup

  1. customThe residue obtained
  2. customchromatographed on silica gel

Sources & evidence

ORD record
ord-ae2574ab53e94c1987a5b532049724f5
Source dataset
uspto-grants-2007_11
Patent number
US07291627B2

Reaction notes

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