Diisopropylethylamine → HCID 59979241, compound

HRID 733326Notes

Reaction equation

HRID 733326 reaction equation
[C:1]([C:3]1[CH:36]=[CH:35][C:6]([CH2:7][C@@:8]2([CH3:34])[N:12]3[C:13]([S:16]([NH:19][C@@H:20]([CH3:24])[C:21]([OH:23])=O)(=[O:18])=[O:17])=[CH:14][N:15]=[C:11]3[N:10]([C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=3)[C:9]2=[O:33])=[CH:5][CH:4]=1)#[N:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[NH2:60][C@@H:61]([C:63]([NH2:65])=[O:64])[CH3:62].C(N(CC)C(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[C:63]([C@H:61]([NH:60][C:21](=[O:23])[C@@H:20]([NH:19][S:16]([C:13]1[N:12]2[C@@:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:36][CH:35]=3)([CH3:34])[C:9](=[O:33])[N:10]([C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=3)[C:11]2=[N:15][CH:14]=1)(=[O:17])=[O:18])[CH3:24])[CH3:62])(=[O:64])[NH2:65]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2775814(2R)-2-Aminopropanamide hydrochlorideHCID 59979225HCID 59979225, compound

Product 1

HCID 59979241HCID 59979241, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonylamino]-propionic acid (see Example 14) (0.05 g, 0.091 mmol) was dissolved in anhydrous DMF (2 mL) and TBTU (0.044 g, 0.137 mmol) was added to the reaction solution. The reaction mixture was stirred at room temperature for 10 min and D-alaninamide hydrochloride (0.017 g, 0.137 mmol) was added to the mixture followed by N,N-diisopropylethylamine (0.039 mL, 0.227 mmol). The reaction mixture was stirred at room temperature for another 15 min. The mixture was then diluted with EtOAc (10 mL) and washed with water, 1 N HCl, saturated NaHCO3 and then water. The organic phase was dried over Na2SO4 and concentrated. The crude product was purified by silica gel preparative thin layer chromatography to afford 0.035 g of the title compound as a white foam (M+1, 618.2).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for another 15 min
  2. washwashed with water, 1 N HCl, saturated NaHCO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel preparative thin layer chromatography

Sources & evidence

ORD record
ord-64c21f6a019e4229ba5fad0815e36e47
Source dataset
uspto-grants-2009_09
Patent number
US07589115B2

Reaction notes

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