9-Fluorenylmethyl chloroformate → HCID 56923947, compound

HRID 926817Notes

Reaction equation

HRID 926817 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.Cl[C:14]([O:16][CH2:17][CH:18]1[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15]>C(=O)(O)[O-].[Na+].O1CCCC1>[C:14]([CH:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=1)[C:10]([OH:12])=[O:11])([O:16][CH2:17][CH:18]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15]

Participants

5

Reactant 2

HCID 343679-Fluorenylmethyl chloroformateHCID 754513-(4-Aminophenyl)propionic acid

Product 1

HCID 56923947HCID 56923947, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

3-(4-aminophenyl)propionic acid (250 mg, 1.5 mmol) in a 10 mL flask was dissolved in a mixture of 10% aqueous sodium bicarbonate (0.32 mL) and tetrahydrofuran (2.2 mL) then cooled in an ice/water bath. 9-fluorenylmethyl chloroformate (422 mg, 1.5 mmol) was added in small portions over 3 min. After 4 h the cooling bath was removed. After additional 4 h at room temperature, the reaction was extracted with deionized water (2 mL) and ethyl ether (2 mL) and the aqueous layer was brought to pH 4 with dilute HCl and placed in a refrigerator. After 1 h solid was collected by vacuum filtration and washed with deionized water then dried under vacuum to give 470 mg of product (80% yield). Mass spectrum (M+Na)+ calcd for C24H21NO4, 400.1. found 410.0.

Workup

  1. temperaturethen cooled in an ice/water bath
  2. customAfter 4 h the cooling bath was removed
  3. extractionthe reaction was extracted with deionized water (2 mL) and ethyl ether (2 mL)
  4. filtrationAfter 1 h solid was collected by vacuum filtration
  5. washwashed with deionized water
  6. customthen dried under vacuum

Sources & evidence

ORD record
ord-26f04d6c76fe4cfca101c83e7942ff98
Source dataset
uspto-grants-2016_03
Patent number
US09289512B2

Reaction notes

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