Triethylamine → HCID 67000241, compound

HRID 560180Notes

Reaction equation

HRID 560180 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:12][C:11](N)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[CH2:27]([O:34][C:35](Cl)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([N:40](CC)CC)C>C1COCC1.O.C(OCC)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([NH2:40])[C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:12][C:11]([C:35]([O:34][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:36])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 58172076HCID 58172076, compound

Product 1

HCID 67000241HCID 67000241, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester (125 mg) was dissolved in 10 mL of THF. To the solution was added 0.5 mL of benzylchloroformate and 0.5 mL of triethylamine. The resulting solution was stirred at ambient temperature overnight (16 h). In the morning the reaction mixture was diluted with 20 mL of water and 20 mL of diethyl ether. The layers were separated and the aqueous layer was washed with 20 mL of diethyl ether. The organic layers were combined and dried over sodium sulfate. After decantation, the solvent was removed on the rotary evaporator. The residue was purified by flash chromatography on silica using 5% EtOAc in hexanes graded to 50% EtOAc in hexanes as the mobile phase to yield 5-(benzyloxycarbonyl)-amino-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester (101 mg). This material was clean by 1H NMR and used in the next step without further purification.

Workup

  1. customThe layers were separated
  2. washthe aqueous layer was washed with 20 mL of diethyl ether
  3. dry with materialdried over sodium sulfate
  4. customAfter decantation, the solvent was removed on the rotary evaporator
  5. customThe residue was purified by flash chromatography on silica using 5% EtOAc in hexanes

Sources & evidence

ORD record
ord-0dd3a0e051f244f1af996d004c758636
Source dataset
uspto-grants-2011_11
Patent number
US08063094B2

Reaction notes

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