Dimethylformamide → HCID 69670343, compound

HRID 1041921Notes

Reaction equation

HRID 1041921 reaction equation
[CH3:1]N(C)C=O.[F:6][C:7]1[CH:16]=[C:15]([C:17]2[N:21]=[C:20]([CH:22]([O:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]4[N:36]=[C:35]([CH:37]([CH3:39])[CH3:38])[O:34][N:33]=4)=[CH:28][CH:27]=3)[CH2:23][CH3:24])[O:19][N:18]=2)[CH:14]=[CH:13][C:8]=1[C:9](OC)=[O:10].[C:40]([O:44][C:45]([NH:47][CH2:48][C:49]([OH:51])=[O:50])=[O:46])([CH3:43])([CH3:42])[CH3:41].CN(C)CCCN=C=[N:59][CH2:60][CH3:61]>CN(C)C1C=CN=CC=1.O>[C:40]([O:44][C:45]([NH:47][CH2:48][C:49]([O:51][CH2:1][C@H:60]([NH:59][C:9](=[O:10])[C:8]1[CH:13]=[CH:14][C:15]([C:17]2[N:21]=[C:20]([CH:22]([O:25][C:26]3[CH:27]=[CH:28][C:29]([C:32]4[N:36]=[C:35]([CH:37]([CH3:39])[CH3:38])[O:34][N:33]=4)=[CH:30][CH:31]=3)[CH2:23][CH3:24])[O:19][N:18]=2)=[CH:16][C:7]=1[F:6])[CH3:61])=[O:50])=[O:46])([CH3:43])([CH3:41])[CH3:42]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 69670594HCID 69670594, compound

Product 1

HCID 69670343HCID 69670343, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

To a dimethylformamide (1.00 mL) solution of the compound obtained in Example 7 that will be described below (69.2 mg, 0.136 mmol), N-(tert-butoxycarbonyl)glycine (47.6 mg, 0.272 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (78.1 mg, 0.405 mmol) and 4-dimethylaminopyridine (1.70 mg, 0.0183 mmol) were added, and the mixture was stirred for one hour at room temperature. Water was added to the reaction mixture, and the mixture was subjected to extraction two times with ethyl acetate, and the organic layer thus obtained was washed sequentially with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (methylene chloride:methanol=99:1→90:10, v/v). Thus, the title compound (91 mg, yield: 100%) was obtained.

Workup

  1. additionwere added
  2. extractionthe mixture was subjected to extraction two times with ethyl acetate
  3. customthe organic layer thus obtained
  4. washwas washed sequentially with water and saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (methylene chloride

Sources & evidence

ORD record
ord-5ac1fa7f1e344f279e122ec120df807b
Source dataset
uspto-grants-2013_10
Patent number
US08557802B2

Reaction notes

Loading…