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Chlorotrimethylsilane → HCID 22870460, compound

HRID 976021
Notes
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Reaction equation

HRID 976021 reaction equation
Cl.Cl.[NH2:3][C@@H:4]([CH2:8]/[CH:9]=[CH:10]/[CH2:11][C@H:12]([NH2:16])[C:13]([OH:15])=[O:14])[C:5]([OH:7])=[O:6].C[Si](Cl)(C)C.[C:22](Cl)([O:24][CH2:25][CH:26]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23]>C[Si](N[Si](C)(C)C)(C)C.ClCCl>[CH:37]1[C:38]2[CH:26]([CH2:25][O:24][C:22]([NH:3][C@@H:4]([CH2:8]/[CH:9]=[CH:10]/[CH2:11][C@H:12]([NH:16][C:22]([O:24][CH2:25][CH:26]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=4[C:33]4[C:38]3=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:23])[C:13]([OH:15])=[O:14])[C:5]([OH:7])=[O:6])=[O:23])[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]=2[CH:34]=[CH:35][CH:36]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 343679-Fluorenylmethyl chloroformateHCID 86750549HCID 86750549, compound

Product 1

HCID 22870460HCID 22870460, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 13838
Hexamethyldisilazane
Solvent

Conditions

Temperature
0 °C

Procedure

(S,S)-2,7-Diamino-E-oct-4-enedioic acid dihydrochloride (1.59 g, 5.8 mmol) was suspended in HMDS (20 ml) and TMSCl and refluxed overnight. The solvents were removed, and the residue was dissolved in anhydrous dichloromethane. This solution was cooled to 0° C. and a solution of FmocCl (3.10 g, 12 mmol) in dichloromethane was added. The solution was stirred for 1 hour at this temperature and overnight at ambient temperature. The solvent was evaporated and the residue dissolved in THF. After addition of 1N aqueous HCl the solution was stirred for two hours, extracted with chloroform and dried (MgSO4). The residue was dissolved in dichloromethane and crystallized by the addition of diethylether.

Workup

  1. customThe solvents were removed
  2. dissolutionthe residue was dissolved in anhydrous dichloromethane
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in THF
  5. additionAfter addition of 1N aqueous HCl the solution
  6. stirringwas stirred for two hours
  7. extractionextracted with chloroform
  8. dry with materialdried (MgSO4)
  9. dissolutionThe residue was dissolved in dichloromethane
  10. customcrystallized by the addition of diethylether

Sources & evidence

ORD record
ord-feac30f1e166451c8b7e4bf428483f7b
Source dataset
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05610141

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes