Ethylmorpholine → N-[[6-methoxy-5-(pentafluoroethyl)-1-naphthalenyl]carbonyl]-N-methylglycine, methyl ester

HRID 364445

反応式

HRID 364445 の反応式
[CH3:1][O:2][C:3]1[C:4]([C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13](O)=[O:14])=[CH:8][CH:7]=[CH:6]2.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[CH3:49][O:50][C:51](=[O:55])[CH2:52][NH:53][CH3:54].C(N1CCOCC1)C>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([C:16]([F:21])([F:22])[C:17]([F:20])([F:19])[F:18])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([N:53]([CH3:54])[CH2:52][C:51]([O:50][CH3:49])=[O:55])=[O:14])=[CH:8][CH:7]=[CH:6]2

参加物

7

反応物 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 139590766-Methoxy-5-(pentafluoroethyl)naphthalene-1-carboxylic acid

生成物 1

HCID 131714821N-[[6-methoxy-5-(pentafluoroethyl)-1-naphthalenyl]carbonyl]-N-methylglycine, methyl ester収率 54.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

The crude 6-methoxy-5-(pentafluoroethyl)-1-naphthalene carboxylic acid (3.65 g, 11.4 mmol), 1-hydroxybenzotriazole (2.31 g, 17.1 mmol), dry distilled dimethylformamide (35 ml) and dicyclohexylcarbodiimide (2.82 g, 13.7 mmol) were stirred at room temperature for 1 hour. The mixture was cooled to 0° C., a solution of sarcosine methyl ester hydrochloride (3.18 g, 22.8 mmol) in dimethylformamide (30 ml) and N-ethyl morpholine (2.92 ml, 22.8 mmol) was added and stirring continued for 2 hours at room temperature. After cooling to 0° C., the precipitate (dicyclohexyl urea) was removed by filtration, the filtrate evaporated and the residue purified by HPLC (ethyl acetate/hexane 1:1, Waters Prep LC 500A). 1.5 g of pure, and 2.5 g of less pure N-[[6-methoxy-5-(pentafluoroethyl)-1-naphthalenyl]carbonyl]-N-methylglycine, methyl ester were obtained. nmr (DMSO): δ2.75 & 3.25 (2s, 3H, N--CH3, rotamers); δ3.75 (s, 3H, OCH3); δ3.97 (s, 3H, OCH3); δ4.35 (broad, 2H, N--CH2 --CO); δ7.7 (m, 5H, Har). ms: m/e 405 (M+), 303, 195, 102.

後処理

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringstirring
  3. waitcontinued for 2 hours at room temperature
  4. temperatureAfter cooling to 0° C.
  5. customthe precipitate (dicyclohexyl urea) was removed by filtration
  6. customthe filtrate evaporated
  7. customthe residue purified by HPLC (ethyl acetate/hexane 1:1, Waters Prep LC 500A)

出典と根拠

ORDレコード
ord-bc8ee403baaf4b9e8c8eaf8efd63030c
出典データセット
uspto-grants-1986_08
特許番号
US04604406

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