1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69739712, compound

HRID 495815Notes

Reaction equation

HRID 495815 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:17])([CH3:16])[CH2:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2N=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[S:39]1[CH:43]=[C:42]([CH2:44][CH:45]([NH:62][CH3:63])[C:46]([N:48]([CH3:61])[C@@H:49]([C:57](=[O:60])[NH:58][CH3:59])[CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:47])[C:41]2[CH:64]=[CH:65][CH:66]=[CH:67][C:40]1=2.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]([CH3:17])([CH3:16])[CH2:10]/[CH:11]=[CH:12]/[C:13](=[O:15])[N:62]([C@@H:45]([C:46](=[O:47])[N:48]([CH3:61])[CH:49]([C:57](=[O:60])[NH:58][CH3:59])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:44][C:42]1[C:41]2[CH:64]=[CH:65][CH:66]=[CH:67][C:40]=2[S:39][CH:43]=1)[CH3:63])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 10847814(2E)-5-(tert-Butyloxycarbonylamino)-5-methylhex-2-enoic acidHCID 53849785HCID 53849785, compound

Product 1

HCID 69739712HCID 69739712, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(2E)-5-(tert-Butyloxycarbonylamino)-5-methylhex-2-enoic acid (0;19 g; 0.78 mmol) was dissolved in methylene chloride (10 mL). 1-Hydroxy-7-azabenzotriazole (0.11 g; 0.78 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.16 g; 0.86 mmol) were added. The reaction mixture was stirred for 15 min at room temperature. 3-(Benzo[b]thiophen-3-yl)-N-methyl-2-methylamino-N-((1R)-1-methylcarbamoyl-2-phenylethyl)propionamide (0.32 g ; 0.78 mmol) was dissolved in methylene chloride (10 mL) and added. Diisopropylethylamine (0.13 mL; 0.78 mmol) was added. The reaction mixture was stirred for 12 hours at room temperature. Methylene chloride (10 mL) was added. The reaction was washed with water (20 mL), an aqueous solution of sodium hydrogen sulfate (10%; 20 mL), an aqueous solution of sodium hydrogen carbonate (saturated; 20 mL) and dried (magnesium sulfate). The solvent was removed in vacuo and the residue was chromatographed on silica (2×20 cm) using ethylacatate/methylene chloride (1:1) as eluent to afford 0.26 g of ((3E)-4-(((1R)-2-(benzo[b]thiophen-3-yl)-1-(methyl-(1-methylcarbamoyl-2-phenylethyl)carbamoyl)ethyl)methylcarbamoyl)-1,1-dimethylbut-3-enyl)carbamic acid tert-butylester.

Workup

  1. additionadded
  2. stirringThe reaction mixture was stirred for 12 hours at room temperature
  3. washThe reaction was washed with water (20 mL)
  4. dry with materialan aqueous solution of sodium hydrogen sulfate (10%; 20 mL), an aqueous solution of sodium hydrogen carbonate (saturated; 20 mL) and dried (magnesium sulfate)
  5. customThe solvent was removed in vacuo
  6. customthe residue was chromatographed on silica (2×20 cm)

Sources & evidence

ORD record
ord-6d9f9a82fdaf4ad3b7ecbf561a3da152
Source dataset
uspto-grants-2005_09
Patent number
US06939880B2

Reaction notes

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