Triethylamine → methyl N-(9-fluorenylcarbonyl)glycinate

HRID 1729247Notes

Reaction equation

HRID 1729247 reaction equation
C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.[CH:18]1[C:30]2[CH:29]([C:31](O)=[O:32])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1.Cl.[NH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38]>C(Cl)Cl.O>[CH:18]1[C:30]2[CH:29]([C:31]([NH:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[O:32])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 748099-CarboxyfluoreneHCID 757711-HydroxybenzotriazoleHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 19011672methyl N-(9-fluorenylcarbonyl)glycinateYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.2 ml of triethylamine and 1.31 g of 1-hydroxybenzotriazole were successively added, under ice-cooling, to a solution of 1.5 g of fluorene-9-carboxylic acid and 0.90 g of methyl glycinate hydrochloride in 50 ml of methylene chloride, followed by further adding 10 minutes later 1.64 g of water-soluble carbodiimide hydrochloride. The resultant mixture was stirred at 0° C. for 0.5 hour and, then at room temperature for 20 hours. The reaction mixture was washed with 5% hydrochloric acid, saturated sodium bicarbonate, and saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by a silica gel column chromatography (eluting solution: chloroform-methanol) to give 1.87 g of methyl N-(9-fluorenylcarbonyl)glycinate.

Workup

  1. washThe reaction mixture was washed with 5% hydrochloric acid, saturated sodium bicarbonate, and saturated saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by a silica gel column chromatography (eluting solution: chloroform-methanol)

Sources & evidence

ORD record
ord-3858955b8c9d42bb87c126ea3f81373a
Source dataset
uspto-grants-1994_07
Patent number
US05332734

Reaction notes

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