2-Methylbenzylamine → HCID 10752313, compound

HRID 1596317Notes

Reaction equation

HRID 1596317 reaction equation
CCN=C=NCCCN(C)C.Cl.[N:13]1(C(OC(C)(C)C)=O)[CH2:20][S:19][CH2:18][C@H:14]1[C:15]([OH:17])=O.[CH3:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH2:32].C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH3:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH:32][C:15]([C@@H:14]1[CH2:18][S:19][CH2:20][NH:13]1)=[O:17]

Participants

6

Reactant 4

HCID 69932-MethylbenzylamineHCID 757711-HydroxybenzotriazoleHCID 688405(4R)-3-[(tert-butoxy)carbonyl]-1,3-thiazolidine-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 10752313HCID 10752313, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDC.HCl (6.30 g, 33.0 mmol) was added to a solution of Boc-Thz-OH (6.99 g, 30 mmol), 2-methylbenzylamine (4.46 ml, 36.0 mmol), and HOBt (4.05 g, 30 mmol) in CH2Cl2 (100 ml) while cooling with ice, and the mixture was stirred overnight. The reaction mixture was washed with 3% Na2CO3 (twice), 1NHCl (once), and 5% NaCl (once) and dried over MgSO4. After filtration and concentration, the residue was dissolved in CH2Cl2 (100 ml). After the addition of methanesulfonic acid MSA (5.86ml, 90mmol), the mixture was stirred for two hours. H2O (150 ml) was added to the reaction mixture and the aqueous layer adjusted to pH 8 with Na2CO3 was extracted with CH2Cl2 (100 ml). The extract was washed with 5% NaCl and dried over MgSO4. After filtration and concentration, the residue was recrystallized from AcOEt/n-hexane to obtain the title compound (6.04 g, 85%).

Workup

  1. temperaturewhile cooling with ice
  2. washThe reaction mixture was washed with 3% Na2CO3 (twice), 1NHCl (once), and 5% NaCl (once) and
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration and concentration
  5. dissolutionthe residue was dissolved in CH2Cl2 (100 ml)
  6. additionAfter the addition of methanesulfonic acid MSA (5.86ml, 90mmol)
  7. stirringthe mixture was stirred for two hours
  8. additionH2O (150 ml) was added to the reaction mixture
  9. extractionwas extracted with CH2Cl2 (100 ml)
  10. washThe extract was washed with 5% NaCl
  11. dry with materialdried over MgSO4
  12. filtrationAfter filtration and concentration
  13. customthe residue was recrystallized from AcOEt/n-hexane

Sources & evidence

ORD record
ord-5572fcee230a481d95d9b8a1f3509c24
Source dataset
uspto-grants-2001_09
Patent number
US06291432B1

Reaction notes

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