Dimethylformamide → HCID 86644639, compound

HRID 1662079Notes

Reaction equation

HRID 1662079 reaction equation
Cl.[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:12]([NH:14][C@H:15]([C:20]([NH:22][C@H:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:21])[CH2:16][CH2:17][CH2:18][NH2:19])=[O:13].CN(C=O)C.[N+](C1C=CC(N[C:50](=[O:59])[O:51][CH2:52][CH:53]2[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]2)=CC=1)([O-])=O.C(N(CC)CC)C>O>[CH:53]1([CH2:52][O:51][C:50]([NH:19][CH2:18][CH2:17][CH2:16][C@@H:15]([C:20]([NH:22][C@H:23]2[CH2:27][CH2:26][CH2:25][C@H:24]2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:21])[NH:14][C:12]([C:4]2[N:3]([CH3:2])[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)=[O:13])=[O:59])[CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 67427929HCID 67427929, compoundHCID 86644629HCID 86644629, compound

Product 1

HCID 86644639HCID 86644639, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of tert-butyl (1R,2S)-2-({N2-[(1-methyl-1H-indol-2-yl)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate hydrochloride (0.41 g) and DMF (4.0 ml) were added cyclohexylmethyl 4-nitrophenylcarbamate (0.28 g) and triethylamine (94 mg) under ice-cooling, followed by stirring at room temperature for 1 hour. To the reaction mixture was added water (10 ml) under ice-cooling, followed by stirring at room temperature for 1 hour. The solid precipitated was collected by filtration, washed with water, and purified by silica gel column chromatography (chloroform/THF=10:1) to obtain tert-butyl (1R,2S)-2-({N5-[(cyclohexylmethoxy)carbonyl]-N2-[(1-methyl-1H-indol-2-yl)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate (0.41 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 1 hour
  4. customThe solid precipitated
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. custompurified by silica gel column chromatography (chloroform/THF=10:1)

Sources & evidence

ORD record
ord-d17e883a76a242ab94e654152de151f8
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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