Tris(hydroxymethyl)aminomethane → HCID 67416503, compound

HRID 906038Notes

Reaction equation

HRID 906038 reaction equation
[CH2:1]([O:5][C:6](Cl)=[O:7])[CH:2]([CH3:4])[CH3:3].CCN(CC)CC.FC(F)(F)C([O-])=O.C([O:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([C:36]2[CH:41]=[CH:40][C:39]([N:42]3[CH2:47][CH2:46][NH2+:45][CH2:44][CH2:43]3)=[CH:38][CH:37]=2)=[O:35])=[CH:29][CH:28]=1)(=O)C.C(O)C(N)(CO)CO>C1COCC1>[OH:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([C:36]2[CH:41]=[CH:40][C:39]([N:42]3[CH2:47][CH2:46][N:45]([C:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:7])[CH2:44][CH2:43]3)=[CH:38][CH:37]=2)=[O:35])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 67414694HCID 67414694, compound

Product 1

HCID 67416503HCID 67416503, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 eq of isobutyl-chloroformate and 3.5 eq of Et3N were added to a solution of 4-[4-({[4-(acetyloxy)phenyl]amino}carbonyl)phenyl]piperazin-1-ium trifluoroacetate in dry THF (0.05 M) and the solution was allowed to stir at RT for 3 h under N2. PS-trisamine resin (excess) was added and the reaction mixture was stirred for 16 h. The resin and a white precipitate were filtered off. Excess aqueous NaOH (1 M) was added to the organic solution and the reaction mixture was stirred for 2 h. The organic solvent was removed in vacuo and aqueous HCl (1 M) was added until precipitation of a white solid that was filtered off, washed and dried in vacuo to afford the title compound (90%).

Workup

  1. stirringthe reaction mixture was stirred for 16 h
  2. filtrationThe resin and a white precipitate were filtered off
  3. additionExcess aqueous NaOH (1 M) was added to the organic solution
  4. stirringthe reaction mixture was stirred for 2 h
  5. customThe organic solvent was removed in vacuo and aqueous HCl (1 M)
  6. additionwas added until precipitation of a white solid
  7. filtrationthat was filtered off
  8. washwashed
  9. customdried in vacuo

Sources & evidence

ORD record
ord-859d96cd98da4a67a35b97eebe50ac09
Source dataset
uspto-grants-2011_09
Patent number
US08012982B2

Reaction notes

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