Dichloromethane → HCID 58473525、化合物

HRID 2282346ノート

反応式

HRID 2282346 の反応式
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.[CH:14]1[C:26]2[CH:25]([CH2:27][O:28][C:29](=[O:108])[NH:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH2:58][CH2:59][O:60][CH2:61][CH2:62][O:63][CH2:64][CH2:65][O:66][CH2:67][CH2:68][O:69][CH2:70][CH2:71][O:72][CH2:73][CH2:74][O:75][CH2:76][CH2:77][O:78][CH2:79][CH2:80][O:81][CH2:82][CH2:83][O:84][CH2:85][CH2:86][O:87][CH2:88][CH2:89][O:90][CH2:91][CH2:92][O:93][CH2:94][CH2:95][O:96][CH2:97][CH2:98][O:99][CH2:100][CH2:101][O:102][CH2:103][CH2:104][C:105](O)=[O:106])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]=2[CH:17]=[CH:16][CH:15]=1.ClCCl>CO>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:105](=[O:106])[CH2:104][CH2:103][O:102][CH2:101][CH2:100][O:99][CH2:98][CH2:97][O:96][CH2:95][CH2:94][O:93][CH2:92][CH2:91][O:90][CH2:89][CH2:88][O:87][CH2:86][CH2:85][O:84][CH2:83][CH2:82][O:81][CH2:80][CH2:79][O:78][CH2:77][CH2:76][O:75][CH2:74][CH2:73][O:72][CH2:71][CH2:70][O:69][CH2:68][CH2:67][O:66][CH2:65][CH2:64][O:63][CH2:62][CH2:61][O:60][CH2:59][CH2:58][O:57][CH2:56][CH2:55][O:54][CH2:53][CH2:52][O:51][CH2:50][CH2:49][O:48][CH2:47][CH2:46][O:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][O:39][CH2:38][CH2:37][O:36][CH2:35][CH2:34][O:33][CH2:32][CH2:31][NH:30][C:29](=[O:108])[O:28][CH2:27][CH:25]2[C:26]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:19]3[C:24]2=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 435310881156914-56-5HCID 51340974Fmoc-N-amido-PEG24-acid

生成物 1

HCID 58473525HCID 58473525、化合物収率 71.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-(4-bromophenoxy)butan-1-amine (21.5 mg, 0.09 mmol), 1-(9H-fluoren-9-yl)-3-oxo-2,7,10,13,16,19,22,25,28,31,34,37,40,43,46,49,52,55,58,61,64,67,70,73,76-pentacosaoxa-4-azanonaheptacontan-79-oic acid (100 mg, 0.073 mmol), and N,N′-dimethylaminopyridine (5.4 mg, 0.044 mmol) were combined in a round bottom flask flushed with nitrogen and charged with a Teflon stirbar. Next 5 mL of anhydrous dichloromethane was added via syringe. N,N-Dicyclohexylcarbodiimide (23 mg, 0.11 mmol) is transferred to a second flask flushed with nitrogen and charged with a stirbar and 5 mL of anhydrous dichloromethane is added via syringe. While stirring the first solution, add the dicyclohexylcarbodiimide solution slowly, dropwise. The reaction is then allowed to proceed overnight. The following day solids from the reaction were filtered off and the filtrate was concentrated onto silica. Column chromatography in methanol and dichloromethane gave a clear thick oil (83.3 mg, 71% yield).

後処理

  1. customflushed with nitrogen
  2. additioncharged with a Teflon stirbar
  3. additionNext 5 mL of anhydrous dichloromethane was added via syringe
  4. customflushed with nitrogen
  5. additioncharged with a stirbar and 5 mL of anhydrous dichloromethane
  6. additionis added via syringe
  7. additionadd the dicyclohexylcarbodiimide solution slowly
  8. filtrationThe following day solids from the reaction were filtered off
  9. concentrationthe filtrate was concentrated onto silica

出典と根拠

ORDレコード
ord-33f267586c3c4a9e9d19671f509d0d26
出典データセット
uspto-grants-2015_09
特許番号
US09139869B2

反応ノート

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