Triethylamine → HCID 178453335, compound

HRID 1450498Notes

Reaction equation

HRID 1450498 reaction equation
[NH:1]1[C:5]([CH2:6][C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[C:10]3[CH2:16][CH2:17][NH2:18])=[N:4][N:3]=[N:2]1.C(N(CC)CC)C.[O:26](C(OC(C)(C)C)=O)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=O>C(Cl)Cl>[C:30]([O:29][C:27]([NH:18][CH2:17][CH2:16][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([CH2:6][C:5]3[NH:1][N:2]=[N:3][N:4]=3)[CH:8]=2)[NH:12][CH:11]=1)=[O:26])([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 178510860HCID 178510860, compound

Product 1

HCID 178453335HCID 178453335, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2-(5-tetrazol-5-ylmethyl-1H-indol-3-yl)ethylamine (1.76 g, 7.27 mmol) in dry CH2Cl2 (40 ml) was added triethylamine (1.5 g, 14.9 mmol) and (BOC)2O(1.9 g, 7.3 mmol) and the mixture stirred for 16 h. The solvent was removed under vacuum and the residue chromatographed on silica-gel eluting with EtOH/Et2O/H2O/NH3 (20:60:8:1) to give the title product (1.6 g, 64%); δ (360 MHz, CD3OD) 1.41 (9H, s, 3 of CH3); 2.87 (2H, t, J=7.4 Hz, CH2); 3.30 (2H, t, J=7.4 Hz, CH2); 4.32 (2H, s, CH2); 6.99 (1H, d, J=8.3 Hz, At--H); 7.04 (1H, s, Ar--H); 7.26 (1H, d, J=8.3 Hz, Ar--H); 7.49 (1H, s, Ar--H).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue chromatographed on silica-gel
  3. washeluting with EtOH/Et2O/H2O/NH3 (20:60:8:1)

Sources & evidence

ORD record
ord-f5a80f47154c4f8a9d4031bcdd2df824
Source dataset
uspto-grants-1997_02
Patent number
US05602163

Reaction notes

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