Triethylamine → HCID 86761393, compound

HRID 1676887Notes

Reaction equation

HRID 1676887 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:28][CH2:29][C:30]#[C:31][CH2:32][OH:33].C(N(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([NH:28][CH2:29][C:30]#[C:31][CH2:32][OH:33])=[O:14])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidHCID 197755314-Aminobut-2-yn-1-ol hydrochloride

Product 1

HCID 86761393HCID 86761393, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[(tert.-butoxycarbonyl)amino]butanoic acid (5.20 g, 25.6 mmol, prepared in analogy to Houssin et al., (1988) Synthesis 3, 259-261) was dissolved in anhydrous tetrahydrofuran (20 mL), carbonyldimidazole (CDI) (4.56 g, 28.1 mmol) was added and the resulting clear solution was stirred at room temperature for 2 h. Then, the primary amine 11 (3.11 g 25.6 mmol) and trietylamine (7.10 mL, 50.9 mmol) were added and stirring was continued at room temperature for 2 h. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel, 40 g, chloroform/ethylacetate 1:1) to give compound 12 (3.59 g, 52%) as a light yellow oil (Rf 0.3, chloroform/ethyl acetate 1:1).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature for 2 h
  3. customThe solvent was removed under reduced pressure
  4. customthe crude product was purified by column chromatography (silica gel, 40 g, chloroform/ethylacetate 1:1)

Sources & evidence

ORD record
ord-82edaf0c838540fba538441988ea1f1b
Source dataset
uspto-grants-2011_08
Patent number
US08008007B2

Reaction notes

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