1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 45377867, compound

HRID 2362014Notes

Reaction equation

HRID 2362014 reaction equation
[CH2:1]([NH:8][C:9](=[O:18])[NH:10][CH2:11][C:12]1([C:15]([OH:17])=O)[CH2:14][CH2:13]1)[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.[NH2:40][C@@H:41]([CH2:64][C:65]1[CH:70]=[CH:69][C:68]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[CH:67][CH:66]=1)[C:42]([N:44]([CH2:56][CH:57]([O:61][CH2:62][CH3:63])[O:58][CH2:59][CH3:60])[CH2:45][C:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48][CH:47]=1)=[O:43]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:1]([NH:8][C:9](=[O:18])[NH:10][CH2:11][C:12]1([C:15]([NH:40][C@@H:41]([CH2:64][C:65]2[CH:70]=[CH:69][C:68]([O:71][C:72]([CH3:74])([CH3:73])[CH3:75])=[CH:67][CH:66]=2)[C:42]([N:44]([CH2:56][CH:57]([O:61][CH2:62][CH3:63])[O:58][CH2:59][CH3:60])[CH2:45][C:46]2[C:55]3[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=3)[CH:49]=[CH:48][CH:47]=2)=[O:43])=[O:17])[CH2:13][CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 24773279HCID 24773279, compoundHCID 53397486HCID 53397486, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 45377867HCID 45377867, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-((3-benzylureido)methyl)cyclopropanecarboxylic acid (Compound VI-1) (182 mg, 0.77 mmol), hydroxybenzotriazol (126 mg, 0.51 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (98 mg, 0.51% mmol) in dichloromethane (1.5 ml) was added a solution of (S)-2-amino-3-(4-tert-butoxyphenyl)-N-(2,2-diethoxyethyl)-N-(naphthalen-1-ylmethyl)propanamide (Compound IV-2) (125 mg, 0.25 mmol) and 4-dimethylaminopyridine (16 mg, 0.13 mmol) in dichloromethane (1.5 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetated (150 ml) and washed with saturated sodium bicarbonate (50 ml), water (10 ml) and brine (15 ml). The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by Purif silica gel column chromatography (eluent: n-hexanae:ethylacetate=50:50 to 0:100) to obtain the title compound (175 mg, 97%).

Workup

  1. additionThe reaction mixture was diluted with ethyl
  2. washwashed with saturated sodium bicarbonate (50 ml), water (10 ml) and brine (15 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by Purif silica gel column chromatography (eluent: n-hexanae:ethylacetate=50:50 to 0:100)

Sources & evidence

ORD record
ord-f880634c6c5d409a9d607ff749b518b1
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

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