3,5-Dimethylaniline → HCID 28213684, compound

HRID 1744708Notes

Reaction equation

HRID 1744708 reaction equation
C([NH:8][C@H:9]([C:11](O)=[O:12])[CH3:10])(OC(C)(C)C)=O.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:29][C:30]1[CH:31]=[C:32]([CH:34]=[C:35]([CH3:37])[CH:36]=1)[NH2:33]>ClCCl>[NH2:8][C@H:9]([CH3:10])[C:11]([NH:33][C:32]1[CH:34]=[C:35]([CH3:37])[CH:36]=[C:30]([CH3:29])[CH:31]=1)=[O:12]

Participants

5

Reactant 3

HCID 79493,5-DimethylanilineHCID 10868DicyclohexylcarbodiimideHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 28213684HCID 28213684, compoundYield 138.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

This compound is an intermediate for the synthesis of the compound of example 6. To the solution of N-Boc-L-alanine (1.000 g, 5.28 mmol) in dichloromethane (10 ml) is added dicyclohexylcarbodiimide (DCC, 1,094 g, 5.28 mmol) in dichloromethane (10 ml). To this mixture is added 3,5-dimethylaniline (0.640 g, 5.28 mmol) in dichloromethane (10 ml). After 16 h of mixing at room temperature, the dicyclohexylurea is recovered on a filter, the filtrate is dry evaporated. 1.41 g (91%) of white powder are obtained, mp 134°–136° C. The material is dissolved in trifluoroacetic acid (5 ml) and the solution is mixed for 30 min. at room temperature. The solution is dry evaporated. The product is dissolved in methanol (10 ml). To this solution dichloromethane (30 ml) is added and the solution is washed with a solution of 1 M (30 ml) sodium carbonate and water (2×30 ml). The organic phase is dry evaporated. 0.64 g (63%) of product are obtained in the form of a brown oil.

Workup

  1. additionAfter 16 h of mixing at room temperature
  2. customthe dicyclohexylurea is recovered on a filter
  3. customthe filtrate is dry
  4. customevaporated

Sources & evidence

ORD record
ord-a2ad9ae1f1264894bdfe653fcdfcca57
Source dataset
uspto-grants-2006_03
Patent number
US07018537B2

Reaction notes

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