Dicyclohexylcarbodiimide → N-[N'-(Fluorenylmethyloxycarbonyl)glycyl]-N-[2-(thymin-1-yl)ethyl]-glycine tert-butyl ester

HRID 54618Notes

Reaction equation

HRID 54618 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][NH:8][CH2:9][CH2:10][N:11]1[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]1=[O:13])([CH3:4])([CH3:3])[CH3:2].[C:21]1([CH2:34][O:35][C:36]([NH:38][CH2:39][C:40](O)=[O:41])=[O:37])[C:33]2[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]=2[CH:24]=[CH:23][CH:22]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]([C:40](=[O:41])[CH2:39][NH:38][C:36]([O:35][CH2:34][C:21]1[C:33]2[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]=2[CH:24]=[CH:23][CH:22]=1)=[O:37])[CH2:9][CH2:10][N:11]1[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]1=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14767770Fluorenylmethoxy-carbonyl-glycineHCID 19959625N-[2-(Thymin-1-yl)ethyl]-glycine tert-butyl ester

Product 1

HCID 86750730N-[N'-(Fluorenylmethyloxycarbonyl)glycyl]-N-[2-(thymin-1-yl)ethyl]-glycine tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 8 (3.78 g; 13 mmol) and N-(fluorenylmethyloxycarbonyl)glycine (5.9 g; 20 mmol) are dissolved in anhydrous N,N-dimethylformamide (160 ml) under a protective atmosphere of argon gas. N,N'-Dicyclohexylcarbodiimide (4.11 g; 20 mmol) is added in portions at 0° C. The mixture is stirred at room temperature for 21 h and the solid which has precipitated is subsequently filtered off with suction. The solution is then concentrated in vacuo, and subsequently distilled repeatedly with toluene, and the crude product is chromatographed on silica gel. (Eluent: toluene/ethanol, 30:1-20:1). Yield: 6.33 g (82%).

Workup

  1. customthe solid which has precipitated
  2. filtrationis subsequently filtered off with suction
  3. concentrationThe solution is then concentrated in vacuo
  4. distillationsubsequently distilled repeatedly with toluene
  5. customthe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-e8b00b43fa464d3d9c3332972aa04cb6
Source dataset
uspto-grants-1997_04
Patent number
US05623049

Reaction notes

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