Triethylamine → HCID 68685886, compound

HRID 2246420Notes

Reaction equation

HRID 2246420 reaction equation
C(OC(=O)[CH2:10][CH2:11][C@@H:12]([C:21]([OH:23])=O)[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])C1C=CC=CC=1.ON1[C:30](=[O:31])CCC1=O.C1(N=C=N[CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)CCCCC1.Cl.[NH:49]1[CH2:53][CH2:52][CH2:51][CH:50]1[C:54]#[N:55].C(N(CC)CC)C.C(Cl)Cl.C1OCC[O:68]C1>>[CH2:30]([O:31][C:10](=[O:68])[CH2:11][CH:12]([NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C:21]([N:49]1[CH2:53][CH2:52][CH2:51][CH:50]1[C:54]#[N:55])=[O:23])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

7

Reactant 6

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 83589L-Glutamic acid, N-((1,1-dimethylethoxy)carbonyl)-, 5-(phenylmethyl) esterHCID 18626912Dioxane methylene chlorideHCID 21864982Pyrrolidine-2-carbonitrile--hydrogen chloride (1/1)

Product 1

HCID 68685886HCID 68685886, compoundYield 80%

Procedure

t-Butoxycarbonyl-L-glutamic acid 5-benzyl ester (A) (0.65 g, 2 mmol) and N-hydroxysuccinimide (HOSu, 0.23 g, 2 mmol) were dissolved in 6 ml of CH2Cl2/4-dioxane (2/1). The solution was cooled in an ice-water bath and dicyclohexylcarbodimide (DCC, 0.45 g, 2.2 mmol) was added with stirring. The reaction mixture was stirred at room temperature for 1 hour and then pyrrolidine-2-carbonitrile hydrochloride (B) (0.27 g, 2 mmol) and triethylamine (Et3N, 0.22 g, 2.2 mmol) were added. After 4 hours at room temperature, DCC was removed by filtration and washed by CH2Cl2. The filtrate and washings were combined and washed with 10% aqueous citric acid and then saturated aqueous NaHCO3, dried over MgSO4, and concentrated in vacuo. Further purification by flash column chromatography (eluted with 5/4/1 hexane/CH2Cl2/EA) afforded compound (C) (80%) as a foam.

Workup

  1. temperatureThe solution was cooled in an ice-water bath
  2. stirringThe reaction mixture was stirred at room temperature for 1 hour
  3. customDCC was removed by filtration
  4. washwashed by CH2Cl2
  5. washwashed with 10% aqueous citric acid
  6. dry with materialsaturated aqueous NaHCO3, dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customFurther purification
  9. washby flash column chromatography (eluted with 5/4/1 hexane/CH2Cl2/EA)

Sources & evidence

ORD record
ord-c3a817eabb6e4dbd88219ca877b3ceb2
Source dataset
uspto-grants-2010_03
Patent number
US07687504B2

Reaction notes

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