Di-p-tolylcarbodiimide → HCID 178426524, compound

HRID 1813887Notes

Reaction equation

HRID 1813887 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:23])[C@H:11]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)N)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([N:27](C(C)C)CC)(C)C.[C:33]1([CH3:49])[CH:38]=[CH:37][C:36]([N:39]=[C:40]=[N:41][C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)=[CH:35][CH:34]=1>CN(C=O)C>[C:33]1([CH3:49])[CH:38]=[CH:37][C:36]([N:39]([CH:11]([CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[C:10]([O:9][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:23])[C:40]([NH:41][C:42]2[CH:43]=[CH:44][C:45]([CH3:48])=[CH:46][CH:47]=2)=[NH:27])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 69763Di-p-tolylcarbodiimideHCID 81531DiisopropylethylamineHCID 45073232L-tryptophan benzyl ester hydrochloride

Product 1

HCID 178426524HCID 178426524, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 mmol of tryptophan benzyl ester hydrochloride was dissolved in 20 ml of DMF and 1.1 mmol of diisopropylethylamine was added. After 10 min, 1.0 mmol of 1,3 di-p-tolylcarbodiimide was added to the stirred solution. The reaction mixture was stirred overnight in room temperature. The precipitated solid was filtered off and washed twice with 1 ml of DMF. To the collected filtrate, 50 ml of water was added. The precipitated solid was collected by filtration and washed with water. The solid was dissolved in ethyl acetate and 0.1 ml of conc. HCl was added. The pure product was precipitated from the solution with ethyl ether. Yield of pure compound=79%.

Workup

  1. filtrationThe precipitated solid was filtered off
  2. washwashed twice with 1 ml of DMF
  3. additionTo the collected filtrate, 50 ml of water was added
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. dissolutionThe solid was dissolved in ethyl acetate
  7. addition0.1 ml of conc. HCl was added
  8. customThe pure product was precipitated from the solution with ethyl ether

Sources & evidence

ORD record
ord-f3d466c8f3b941adb6358af8846a5256
Source dataset
uspto-grants-2005_04
Patent number
US06875759B1

Reaction notes

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