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

HRID 1926182Notes

Reaction equation

HRID 1926182 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:53])[CH2:51][NH2:52]>[Cl-].[Na+].O.CN(C=O)C>[CH3:48][O:49][C:50](=[O:53])[CH2:51][NH:52][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 122755Glycine methyl ester hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 579720572-(2-(9H-fluoren-9-ylidene)acetamido)acetic acid methyl esterYield 88%

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), hydroxybenzo-triazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and glycine methyl ester hydrochloride (151.8 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 (256 mg, 88% yield) as a white solid. LC-MS (m/z) 294 (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-9f580220d0eb425f85a253dd4f01432a
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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