Triethylamine → HCID 66637482, compound

HRID 1093920Notes

Reaction equation

HRID 1093920 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:12])[CH2:6][NH:7][C:8](=[O:11])[CH2:9][NH2:10])[CH3:3].C(N(CC)CC)C.O.O.[C:22]([O:26][C:27]([NH:29][C@H:30]([C:38](O)=[O:39])[CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].O.ON1C2C=CC=CC=2N=N1.Cl.CN(CCCCN=C=NCC)C>O1CCCC1>[CH2:2]([O:4][C:5](=[O:12])[CH2:6][NH:7][C:8](=[O:11])[CH2:9][NH:10][C:38](=[O:39])[C@H:30]([CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:28])[CH3:3]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 2827263ethyl 2-(2-aminoacetamido)acetate hydrochlorideHCID 66637966HCID 66637966, compoundHCID 86630335HCID 86630335, compound

Product 1

HCID 66637482HCID 66637482, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 289.4mg (1.47 mmol) of glycyl-glycine ethyl ester hydrochloride in anhydrous tetrahydrofuran (5 mL), 155.9 mg(1.54 mmol) of triethylamine, 451.5 mg (1.47 mmol) of N-t-butoxycarbonyl-β-cyclohexyl-L-alanine dihydrate, 205.3 mg (1.52 mmol) of 1-hydroxybenzotriazole hydrate, and 292.7 mg (1.53 mmol) of 1-[3-(dimethylaminomethyl)propyl]-3-ethylcarbodiimide hydrochloride were added sequentially with stirring under ice cooling. After the mixture was stirred for 1 hour, the reaction mixture was stirred at room temperature for 0.5 hour. The reaction mixture was concentrated under reduced pressure, chloroform (30 mL) was added to the residues, and the solution was washed sequentially with 0.5M hydrochloric acid (3×5 mL), water (3×5 mL) and 5% aqueous sodium hydrogencarbonate solution (3 ×5 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure , whereby 570 mg of a crude product was obtained. The crude product was purified by column chromatography on alumina (alumina 2 g, chloroform), to give 552.8 mg of N-t-butoxycarbonyl-β-cyclohexyl-L-alanyl-glycyl-glycine ethyl ester (yield 91%) as a colorless crystalline powder.

Workup

  1. stirringAfter the mixture was stirred for 1 hour
  2. stirringthe reaction mixture was stirred at room temperature for 0.5 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure, chloroform (30 mL)
  4. additionwas added to the residues
  5. washthe solution was washed sequentially with 0.5M hydrochloric acid (3×5 mL), water (3×5 mL) and 5% aqueous sodium hydrogencarbonate solution (3 ×5 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customwhereby 570 mg of a crude product was obtained
  9. customThe crude product was purified by column chromatography on alumina (alumina 2 g, chloroform)

Sources & evidence

ORD record
ord-fb53f48cd26c485995c3098b710e03a2
Source dataset
uspto-grants-2012_03
Patent number
US08133864B2

Reaction notes

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