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 1828977Notes

Reaction equation

HRID 1828977 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-a1ee38befe5c49129f8c5147e5223e7b
Source dataset
uspto-grants-2006_06
Patent number
US07060847B2

Reaction notes

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