Dimethylformamide → HCID 131726614, compound

HRID 1178302Notes

Reaction equation

HRID 1178302 reaction equation
C1(N=C=N[CH:10]2[CH2:15]CCCC2)CCCCC1.[OH:16][C@@H:17]1[C:22]2=[C:23]3[C:32](=[C:33]([O:35][CH3:36])[CH:34]=[C:21]2[O:20][C:19]([CH3:44])([CH3:43])[C@@H:18]1[OH:45])[C:31](=[O:37])[C:30]1[C:25](=[CH:26][CH:27]=[C:28]2[CH:41]=[CH:40][CH:39]=[CH:38][C:29]2=1)[N:24]3[CH3:42].[C:46]([O:50][C:51]([NH:53][CH2:54][C:55]([OH:57])=O)=[O:52])([CH3:49])([CH3:48])[CH3:47].CN(C)C=[O:61]>>[C:46]([O:50][C:51]([NH:53][CH2:54][C:55]([O:45][C@H:18]1[C:19]([CH3:43])([CH3:44])[O:20][C:21]2[C:22](=[C:23]3[C:32](=[C:33]([O:35][CH3:36])[CH:34]=2)[C:31](=[O:37])[C:30]2[C:25](=[CH:26][CH:27]=[C:28]4[CH:41]=[CH:40][CH:39]=[CH:38][C:29]4=2)[N:24]3[CH3:42])[C@H:17]1[O:16][C:15](=[O:61])[CH3:10])=[O:57])=[O:52])([CH3:47])([CH3:48])[CH3:49]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 11697098HCID 11697098, compound

Product 1

HCID 131726614HCID 131726614, compound

Conditions

Temperature
0 °C

Procedure

Slowly add 0.6 mmol of dicyclohexylcarbodiimide to a solution, at 0° C., of 0.5 mmol of the compound of Example 4 and 0.5 mmol of 2-[(tert-butoxycarbonyl)amino]acetic acid in 10 ml of dimethylformamide. The reaction mixture is maintained at 0° C. for 5 hours and then at ambient temperature for 16 hours. After filtration and evaporation under reduced pressure, the residue is dissolved in 2 ml of anhydrous pyridine; 2 ml of acetic anhydride are added, and the mixture is stirred for 48 hours at ambient temperature and in the dark. After concentrating the reaction mixture under reduced pressure, chromatography of the residue over silica gel (dichloromethane) allows the expected product to be isolated.

Workup

  1. customat 0° C.
  2. filtrationAfter filtration and evaporation under reduced pressure
  3. dissolutionthe residue is dissolved in 2 ml of anhydrous pyridine
  4. addition2 ml of acetic anhydride are added
  5. concentrationAfter concentrating the reaction mixture under reduced pressure, chromatography of the residue over silica gel (dichloromethane)
  6. customto be isolated

Sources & evidence

ORD record
ord-82533d9aa5d44d6c8eec9e0ec6ef98ef
Source dataset
uspto-grants-2007_10
Patent number
US07276512B2

Reaction notes

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