1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44345100, compound

HRID 2302281Notes

Reaction equation

HRID 2302281 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[CH:7]([NH:10][C:11](=[O:17])[C@@H:12]([NH2:16])[CH:13]([CH3:15])[CH3:14])[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[C:4](=[O:22])[N:3]1[CH:23]([CH3:25])[CH3:24].[F:26][C:27]1[CH:28]=[C:29]([CH2:34][C:35](O)=[O:36])[CH:30]=[C:31]([F:33])[CH:32]=1.CN(C)CCCN=C=NCC>ClCCl>[F:26][C:27]1[CH:28]=[C:29]([CH2:34][C:35]([NH:16][C@@H:12]([CH:13]([CH3:15])[CH3:14])[C:11]([NH:10][CH:7]2[C:6]3[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=3[C:4](=[O:22])[N:3]([CH:23]([CH3:25])[CH3:24])[N:2]([CH3:1])[C:8]2=[O:9])=[O:17])=[O:36])[CH:30]=[C:31]([F:33])[CH:32]=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1454243,5-Difluorophenylacetic acidHCID 70060485HCID 70060485, compound

Product 1

HCID 44345100HCID 44345100, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3,4,5-tetrahydro-3-methyl-5(R,S)-[[(2S)-2-amino-3-methyl-1-oxobutyl]amino]-2-(1-methylethyl)-1H-2,3-benzodiazepin-1,4-dione (IIA, 1.44 mL, 0.28 mmol, 0.2 M solution in dichloromethane) in dichloromethane (2 mL) was added the solution of 3,5-difluorophenyl acetic acid (X, 2.16 mL, 0.43 mmol, 0.2 M solution in dichloromethane) and N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide polymer (0.72 g, 1.00 mmol) (Desai, et al., Tet. Lett, 1993, 34(48), 7685-7688). The resulting mixture was shaken on the shaker for 18 h and the resin was filtered off and washed with dichloromethane (2×1 mL). The combined solvent was collected and evaporated and product was analyzed by HPLC using the column YMC S7 C18 (3.0×50 mm) with a flow rate of 5.0 mL/min and gradient time of 2.0 min., starting with solvent A (10% MeOH—90% H2O—0.1% TFA), and ending with solvent B (90% MeOH—10% H2O—0.1% TFA). (70% yield).

Workup

  1. filtrationthe resin was filtered off
  2. washwashed with dichloromethane (2×1 mL)
  3. customThe combined solvent was collected
  4. customevaporated
  5. customwith a flow rate of 5.0 mL/min and gradient time of 2.0 min.

Sources & evidence

ORD record
ord-18a95b45400d402eb47212c8ff9be9ee
Source dataset
uspto-grants-2002_08
Patent number
US06432944B1

Reaction notes

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