Tetrahydrofuran → 843666-31-9

HRID 1434502Notes

Reaction equation

HRID 1434502 reaction equation
[C:1]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O-:20])=[O:19].C1COCC1.CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(O[N:57]1[C:62](=[O:63])[CH2:61][CH2:60][C:58]1=[O:59])=[N+](C)C)C>CN(C=O)C>[C:18]([O:20][N:57]1[C:62](=[O:63])[CH2:61][CH2:60][C:58]1=[O:59])(=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 27282474HCID 27282474, compound

Product 1

HCID 58419211843666-31-9Yield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Mono-benzyl octadecandioate was dissolved in DMF (3.5 mL) and THF (7 mL) and cooled with ice bath. DIEA (0.103 mL) and TSTU were added and the mixture was stirred 1 h at ice bath and at RT overnight. The solvent was evaporated in vacuo and the residue was dissolved in AcOEt and washed twice with 0.2 N HCl, saturated NaHCO3, dried, filtered and evaporated to dryness to give succinimidyl mono-benzyl octadecandioate (0.25 g, 100%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in AcOEt
  3. washwashed twice with 0.2 N HCl, saturated NaHCO3
  4. customdried
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-4e1c884e98464aa898ba4db1e76dbc33
Source dataset
uspto-grants-2009_11
Patent number
US07615532B2

Reaction notes

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