Water → N,N'-bis-(S-benzoylmercaptoacetyl)-1,3-diaminoacetone

HRID 1900214Notes

Reaction equation

HRID 1900214 reaction equation
[C:1]([S:9][CH2:10][C:11](C1CC(=O)N(O)C1=O)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:21].Cl.[NH2:23][CH2:24][C:25]([CH2:27][NH2:28])=[O:26].C(N([CH2:34][CH3:35])CC)C.[OH2:36]>O1CCOCC1>[C:1]([S:9][CH2:34][C:35]([NH:23][CH2:24][C:25]([CH2:27][NH:28][C:11](=[O:12])[CH2:10][S:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:26])=[O:36])(=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 162116331,3-Diaminopropan-2-one hydrate hydrochlorideHCID 86749986benzoylmercaptoacetyl-N-hydroxysuccinimide

Product 1

HCID 57223051N,N'-bis-(S-benzoylmercaptoacetyl)-1,3-diaminoacetoneYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirring solution of (492 g, 1.68 mmoles) benzoylmercaptoacetyl-N-hydroxysuccinimide and (150 mg, 0.84 mmoles) 1,3-diaminoacetone hydrochloride monohydrate in (15 mL) dioxane was added (850 mg, 8.40 mmoles) triethylamine. The reaction stirred 3.5 days followed by rotavapping off the dioxane to a yellow oil and adding (3 mL) water to a yellow solid. The solid was crushed, filtered, washed with water, and dried in vacuo yielding 242 mg, 65% N,N'-bis-(S-benzoylmercaptoacetyl)-1,3-diaminoacetone (m.p. 134°-140° C.).

Workup

  1. customThe solid was crushed
  2. filtrationfiltered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-684c9cd268af412e8a0c85300f7d4869
Source dataset
uspto-grants-1996_11
Patent number
US05574140

Reaction notes

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