Diisopropylethylamine → HCID 178501651, compound

HRID 574665Notes

Reaction equation

HRID 574665 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:18][C:19]([C:21]2[C:22]([OH:30])=[N:23][C:24]([C:27](O)=[O:28])=[N:25][CH:26]=2)=[O:20])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.Cl.[NH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CS(C)=O>[CH3:37][O:36][C:34](=[O:35])[CH2:33][NH:32][C:27]([C:24]1[N:23]=[C:22]([OH:30])[C:21]([C:19](=[O:20])[NH:18][CH:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:26][N:25]=1)=[O:28]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178491171HCID 178491171, compound

Product 1

HCID 178501651HCID 178501651, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The mixture of compound 2-17-e (2.5 g, 6.1 mmol), methyl 2-aminoacetate hydrochloride (0.92 g, 7.3 mmol), TBTU (2.4 g, 7.3 mmol), DIPEA (1.6 g, 12.2 mmol) in DMSO (15 mL) and stirred at the ambient temperature overnight. Ice-water was then added to the reaction mixture and filtered. The cake was purified by column chromatography with DCM:MeOH=100:1˜50:1 to obtain the product, 2-17-f, (630 mg, 22%). LC-MS: (M+H)+ 481.

Workup

  1. filtrationfiltered
  2. customThe cake was purified by column chromatography with DCM
  3. customMeOH=100:1˜50:1 to obtain the product, 2-17-f, (630 mg, 22%)

Sources & evidence

ORD record
ord-eaf7856fc538404ebf132ac11e86d4d1
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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