Diisopropylethylamine → HCID 178472777, compound

HRID 574668Notes

Reaction equation

HRID 574668 reaction equation
[OH:1][C:2]1[C:7]([C:8](=[O:21])[NH:9][CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[CH:6][N:5]=[C:4]([C:22]([OH:24])=O)[N:3]=1.Cl.[NH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].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>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][NH:26][C:22]([C:4]1[N:3]=[C:2]([OH:1])[C:7]([C:8](=[O:21])[NH:9][CH2:10][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][CH:20]=2)=[CH:6][N:5]=1)=[O:24])[CH3:32]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178524891HCID 178524891, compound

Product 1

HCID 178472777HCID 178472777, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The mixture of step D product, 2-20-e, (2.5 g, 7.7 mmol), ethyl 2-aminoacetate hydrochloride (1.29 g, 9.3 mmol), TBTU (2.98 g, 9.3 mmol), DIPEA (2.0 g, 15.5 mmol) in DMSO (20 mL) and stirred at the ambient temperature overnight. Then the reaction mixture was added ice-water (40 mL), extracted with DCM (30 mL×2). The organic phase was concentrated to give a residue, which was purified by column chromatography with DCM:MeOH=150:1 to obtain 2-20 (330 mg, 11%). 1H NMR (300 MHz, DMSO-d6): δ 1.18-1.22 (t, J=6 Hz, 3H), 4.0-4.02 (d, J=6 Hz, 2H), 4.11-4.14 (q, J=6.0 Hz, 2H), 5.0-5.02 (d, J=6.0 Hz, 1H), 7.48-7.57 (m, 4H), 7.87 (m, 3H), 8.55 (br s, 1H), 9.48 (m, 1H), 9.87 (br s, 1H), 13.54 (br s, 1H). LC-MS: (M+H)+ 409.

Workup

  1. extractionextracted with DCM (30 mL×2)
  2. concentrationThe organic phase was concentrated
  3. customto give a residue, which
  4. customwas purified by column chromatography with DCM

Sources & evidence

ORD record
ord-fe315fc505be496a93d4f388d364c482
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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