1,1'-Carbonyldiimidazole → HCID 10708152, compound

HRID 2255219Notes

Reaction equation

HRID 2255219 reaction equation
[CH3:1][NH:2][C:3](=[O:16])[C@H:4]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5].[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18]>C(Cl)Cl>[OH:18][CH2:17][CH2:1][NH:2][C:3](=[O:16])[C@H:4]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 1450557553708-63-7

Product 1

HCID 10708152HCID 10708152, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The hydrochloride salt of L-tryptophan 2-hydroxyethylamide was prepared and coupled with 3 as described for the hydrochloride salt of L-tryptophan methylamide in Example 1 except that 3 was activated with 1,1'-carbonyldiimidazole for 20 minutes in methylene chloride at room temperature. The crude product was a mixture of 0.7 g (67% yield) of the diastereoisomers 12A,B: Rf (C) 12A 0.38, Rf (C) 12B 0.19.

Workup

  1. additiona mixture of 0.7 g (67% yield) of the diastereoisomers

Sources & evidence

ORD record
ord-2dccda887c9547898a1c61050ede7f84
Source dataset
uspto-grants-1993_08
Patent number
US05239078

Reaction notes

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