Dichloromethane → HCID 58473525, compound

HRID 1254963Notes

Reaction equation

HRID 1254963 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 58473525HCID 58473525, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a098242281e947298054f494759935b3
Source dataset
uspto-grants-2013_06
Patent number
US08455613B2

Reaction notes

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