Tris(hydroxymethyl)aminomethane → HCID 21927935, compound

HRID 585558Notes

Reaction equation

HRID 585558 reaction equation
N=C=N.[C:4]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14]C(O)=O)=[O:10])([CH3:7])([CH3:6])[CH3:5].C1C=CC2N([OH:27])N=NC=2C=1.C([N:35]1[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45])[CH2:37][CH2:36]1)C1C=CC=CC=1.C(O)C(N)(CO)CO>ClCCl>[C:4]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([N:35]1[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45])[CH2:37][CH2:36]1)=[O:27])=[O:10])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidHCID 15147569HCID 15147569, compound

Product 1

HCID 21927935HCID 21927935, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of PS-carbodiimide (1.7 g, 1.5 mmoles) in dichloromethane (2 mL) was added 4-(tert-butoxycarbonylamino)butyric acid (305 mg, 1.5 mmoles) and HOBT (230 mg, 1.7 mmoles). After 20 min 186 mg of methyl 4-(4-benzylpiperazin-1-yl)butanoate (186 mg, 1.0 mmol) was added to the reaction mixture and stirred 24 h. PS-trisamine (1.08 g, 5 eq.) was added and stirred 16 h. The reaction mixture was filtered and evaporated to afford methyl 4-{4-[N-(tert-butoxycarbonyl)-beta-alanyl]piperazin-1-yl}butanoate (290 mg, 77%).

Workup

  1. stirringstirred 16 h
  2. filtrationThe reaction mixture was filtered
  3. customevaporated

Sources & evidence

ORD record
ord-e7ad448fdba54c518fb8859e5035cd9e
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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