9-Fluorenylmethyl chloroformate → (9H-Fluoren-9-yl)methyl decyl(2-oxoethyl)carbamate

HRID 966458ノート

反応式

HRID 966458 の反応式
C(CCCCCCCCCCN)C=C.C(N(CC)C(C)C)(C)C.ClC([O:27][CH2:28][CH:29]1C2C=CC=CC=2C2C1=CC=CC=2)=O.[C:42]([NH:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69]CC=C)([O:44][CH2:45][CH:46]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[C:52]2[C:47]1=[CH:48][CH:49]=[CH:50][CH:51]=2)=[O:43]>ClCCl>[C:42]([N:59]([CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH3:69])[CH2:29][CH:28]=[O:27])([O:44][CH2:45][CH:46]1[C:47]2[C:52](=[CH:53][CH:54]=[CH:55][CH:48]=2)[C:51]2[C:58]1=[CH:57][CH:56]=[CH:49][CH:50]=2)=[O:43]

参加物

6

反応物 4

HCID 343679-Fluorenylmethyl chloroformate4 回HCID 81531DiisopropylethylamineHCID 53801489HCID 53801489、化合物HCID 69732531HCID 69732531、化合物

生成物 1

HCID 10070832(9H-Fluoren-9-yl)methyl decyl(2-oxoethyl)carbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
5 °C

実験手順

A three-necked, 500 mL round bottom flask equipped with a thermometer, mechanic stirrer and an addition funnel was purged with nitrogen and charged with N-allyldecylamine (˜0.11 mol) in dichloromethane from step a (210 mL) and N,N-diisopropylethylamine (20.0 mL, 14.8 g, 0.113 mol). The mixture was cooled in a 5° C. ice bath and a solution of 9-fluorenylmethyl chloroformate (25.6 g, 0.099 mol) dissolved in dichloromethane (50 mL) was added dropwise (total volume approximately 330 mL). The reaction was exothermic and the internal temperature was controlled below 10° C. throughout the 9-fluorenylmethyl chloroformate addition. The reaction mixture was warmed to 21° C. when the addition was finished, and monitored by the disappearance of 9-fluorenylmethyl chloroformate and the formation of N-FMOC-N-allyldecylamine using HPLC (retention time for FMOC-chloride=3.08 min; retention time for product=7.96 min). The reaction mixture was washed with 0.01 N HCl (100 mL). The organic layer was collected and used without further purification.

後処理

  1. customA three-necked, 500 mL round bottom flask equipped with a thermometer, mechanic stirrer and an addition funnel
  2. customwas purged with nitrogen
  3. additionwas added dropwise (total volume approximately 330 mL)
  4. temperatureThe reaction mixture was warmed to 21° C. when
  5. additionthe addition
  6. washThe reaction mixture was washed with 0.01 N HCl (100 mL)
  7. customThe organic layer was collected
  8. customused without further purification

出典と根拠

ORDレコード
ord-a433cb9279ff41d8b77458c64a7f7675
出典データセット
uspto-grants-2005_10
特許番号
US06951963B2

反応ノート

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