Triethylamine → 8-(2-(9H-fluoren-9-ylidene)acetamido)octanoic acid methyl ester

HRID 1926204Notes

Reaction equation

HRID 1926204 reaction equation
[CH:1]1[C:13]2[C:12](=[CH:14][C:15](O)=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.Cl.[CH3:48][O:49][C:50](=[O:59])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][NH2:58]>[Cl-].[Na+].O.CN(C=O)C>[CH3:48][O:49][C:50](=[O:59])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][NH:58][C:15](=[O:16])[CH:14]=[C:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 967929H-Fluoren-9-ylideneacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12878164Methyl 8-aminooctanoate hydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 579720548-(2-(9H-fluoren-9-ylidene)acetamido)octanoic acid methyl esterYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-(9H-fluoren-9-ylidene)acetic acid (222 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (394 mg, 2 mmol), hydroxyl-benzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and 8-aminocaprylic acid methyl ester hydrochloride (251 mg, 1.2 mmol) were added. The mixture was stirred for 24 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (328 mg, 87% yield) as a white solid. LC-MS (m/z) 378 (M+1).

Workup

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-34df6da984bd426099f2576df1f5cf8d
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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