2-Dimethylaminopyridine → HCID 86663950, compound

HRID 576883Notes

Reaction equation

HRID 576883 reaction equation
[CH2:1]([NH:8][C:9](=[O:16])[NH:10][CH2:11][CH2:12][C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH2:39]([O:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][C@H:54]([N:65]([CH3:67])[NH2:66])[C:55]([O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)=[O:56])=[CH:49][CH:48]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.CN(C1C=CC=CN=1)C>ClCCl.C(OCC)(=O)C>[CH2:39]([O:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][C@H:54]([N:65]([CH3:67])[NH:66][C:13](=[O:15])[CH2:12][CH2:11][NH:10][C:9]([NH:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:16])[C:55]([O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)=[O:56])=[CH:49][CH:48]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

8

Reactant 5

HCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 16227348N-(Benzylcarbamoyl)-beta-alanineHCID 86663947HCID 86663947, compound

Product 1

HCID 86663950HCID 86663950, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3-benzylureido)propanoic acid (Compound VIII-1) 267 mg (1.20 mmol) in dichloromethane 5 ml, N-hydroxybenzotriazole 203 mg (1.50 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 288 mg (1.50 mmol) were added and the mixture was stirred at room temperature for 0.5 hr. (S)-benzyl 3-(4-(benzyloxy)phenyl)-2-(1-methylhydrazinyl)propanoate (Compound XVIII-1) 390 mg (1.00 mmol) and a solution of dimethylaminopyridine 61 mg (0.50 mmol) in dichloromethane 1 ml were added to the reaction mixture and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was diluted with ethyl acetate 50 ml and washed with saturated sodium bicarbonate solution 50 ml twice, water 50 ml twice and brine 50 ml and the organic phase was dried over magnesium sulfate and filtered. The mother solution was concentrated in vacuo and the residue was purified on silica gel column chromatography (Merck 60N spherical, neutral elution by chloroform:methanol=100:0 to 95:5) to obtain the title compound 0.31 g (52.0%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hrs
  2. washwashed with saturated sodium bicarbonate solution 50 ml twice
  3. dry with materialwater 50 ml twice and brine 50 ml and the organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe mother solution was concentrated in vacuo
  6. customthe residue was purified on silica gel column chromatography (Merck 60N spherical, neutral elution by chloroform:methanol=100:0 to 95:5)

Sources & evidence

ORD record
ord-28b18e8f2c8b43518081154c8ff81df0
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

Loading…