1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-N-benzyl-2-(2-(3-benzylureidooxy)acetamido)-N-(2,2-diethoxyethyl)propanamide

HRID 2362022Notes

Reaction equation

HRID 2362022 reaction equation
[CH2:1]([NH:8][C:9](=[O:16])[NH:10][O:11][CH2:12][C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C.[NH2:38][C@@H:39]([CH3:58])[C:40]([N:42]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:43][CH:44]([O:48][CH2:49][CH3:50])[O:45][CH2:46][CH3:47])=[O:41]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:51]([N:42]([CH2:43][CH:44]([O:45][CH2:46][CH3:47])[O:48][CH2:49][CH3:50])[C:40](=[O:41])[C@@H:39]([NH:38][C:13](=[O:15])[CH2:12][O:11][NH:10][C:9]([NH:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:16])[CH3:58])[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 533974882-((3-Benzylureido)oxy)acetic acidHCID 66644890(S)-2-amino-N-benzyl-N-(2,2-diethoxyethyl)propanamideHCID 178418300HCID 178418300, compound

Product 1

HCID 86658809(S)-N-benzyl-2-(2-(3-benzylureidooxy)acetamido)-N-(2,2-diethoxyethyl)propanamideYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(3-benzylureidooxy)acetic acid (Compound VI-6) (53.8 mg, 0.24 mmol) and hydroxybenzotriazol (40.5 mg, 0.3 mmol) in dichloromethane (1 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (57.5 mg, 0.3 mmol) and 4-dimethylaminopyridine (2.4 mg, 0.02 mmol) and the mixture was stirred at room temperature for 0.5 hr. A solution of (S)-2-amino-N-benzyl-N-(2,2-diethoxyethyl)propanamide (Compound IV-19) (58.9 mg, 0.2 mmol) in dichloromethane (1 ml) was added to the reaction mixture and the mixture was stirred at room temperature for 18 hr. The reaction mixture was washed with sat. NaHCO3 aq. (1 ml), water (1 ml) and brine (1 ml). The organic layer was filtered on Celite (1 g) and magnesium sulfate (150 mg). The filtrate was concentrated in vacuo and the residue was purified with PTLC (development solvent: chloroform:methanol=98:2) to obtain the titled compound (60 mg, 80%).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hr
  2. washThe reaction mixture was washed with sat. NaHCO3 aq. (1 ml), water (1 ml) and brine (1 ml)
  3. filtrationThe organic layer was filtered on Celite (1 g) and magnesium sulfate (150 mg)
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified with PTLC (development solvent: chloroform:methanol=98:2)

Sources & evidence

ORD record
ord-a70a9a2971d04542b8331d57683a09f2
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

Loading…