1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(5-{2-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-propyl}-benzo[1,3]dioxol-2-ylmethyl)-succinamic acid 2,5-dioxo-pyrrolidin-1-yl ester

HRID 2099717Notes

Reaction equation

HRID 2099717 reaction equation
[CH2:1]([N:3]([C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH:4]([CH3:24])[CH2:5][C:6]1[CH:23]=[CH:22][C:9]2[O:10][CH:11]([CH2:13][NH:14][C:15](=[O:21])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])[O:12][C:8]=2[CH:7]=1)[CH3:2].O[N:32]1[C:36](=[O:37])[CH2:35][CH2:34][C:33]1=[O:38].C(N=C=NCCCN(C)C)C>ClCCl>[O:38]=[C:33]1[CH2:34][CH2:35][C:36](=[O:37])[N:32]1[O:19][C:18](=[O:20])[CH2:17][CH2:16][C:15]([NH:14][CH2:13][CH:11]1[O:10][C:9]2[CH:22]=[CH:23][C:6]([CH2:5][CH:4]([N:3]([CH2:1][CH3:2])[C:25](=[O:30])[C:26]([F:28])([F:29])[F:27])[CH3:24])=[CH:7][C:8]=2[O:12]1)=[O:21]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 21966323N-(5-[2-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-propyl}-benzo[1,3]dioxol-2-ylmethyl)-succinamic acid

Product 1

HCID 86595989N-(5-{2-[ethyl-(2,2,2-trifluoro-acetyl)-amino]-propyl}-benzo[1,3]dioxol-2-ylmethyl)-succinamic acid 2,5-dioxo-pyrrolidin-1-yl esterYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 150 mg (0.34 mmol) of 2K was added 15 mL of dichloromethane (distilled over CaH2) followed by 99 mg (0.86 mmol) of N-hydroxysuccinimide and 166 mg (0.86 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide. The reaction mixture was allowed to stir at room temperature under argon atmosphere for 18 hours. The reaction mixture was diluted with an additional 40 mL of dichloromethane and washed with 2×25 mL of water, 3×25 mL of saturated sodium bicarbonate, and 2×25 mL of water. The organic layer was dried (Na2SO4) and concentrated to dryness to give 154 mg (0.29 mmol, 84%) of 2L as a white solid (M+Na, 552).

Workup

  1. washwashed with 2×25 mL of water, 3×25 mL of saturated sodium bicarbonate, and 2×25 mL of water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8a008b2f88bb497db4f2f315dc27a2ac
Source dataset
uspto-grants-2009_08
Patent number
US07569676B2

Reaction notes

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