Diisopropylethylamine → HCID 68669056, compound

HRID 1161952Notes

Reaction equation

HRID 1161952 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12](O)=O)[C:7](=[O:15])[C:6]1=[O:16])[CH2:2][CH2:3][CH3:4].[C:17]([O:21][C:22]([NH:24][C@@:25]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([CH3:30])[C:26]([NH:28][NH2:29])=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18].Cl.CN(C)CCCN=C=NCC.[OH:50]N1C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[C:17]([O:21][C:22]([NH:24][C@:25]([CH3:30])([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]([NH:28][NH:29][CH2:12][C:11]([N:8]1[CH2:9][CH2:10][N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6](=[O:16])[C:7]1=[O:15])=[O:50])=[O:27])=[O:23])([CH3:18])([CH3:19])[CH3:20]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11160520HCID 11160520, compound2×HCID 57513160HCID 57513160, compound2×

Product 1

HCID 68669056HCID 68669056, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4-butyl-2,3-dioxopiperazin-1-yl)acetic acid (Intermediate F, 142 mg, 0.62 mmol), (R)-2-tert-butoxycarbonylamino-2-benzylpropanehydrazide (Intermediate B, 225 mg, 0.77 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (131 mg, 0.68 mmol), 1-hydroxy-7-azabenzotriazole (93 mg, 0.68 mmol) and diisopropylethylamine (0.12 mL, 0.68 mmol) in 6.2 mL DMF was stirred at rt overnight. The reaction mixture was diluted with EtOAc and washed with water and brine. Drying, solvent evaporation and flash chromatography (silica gel, 0-10% MeOH/CH2Cl2) gave 1-((2-((R)-2-tert-butoxycarbonylamino-2-methyl-3-phenylpropanoyl)hydrazino)acetyl)-4-butylpiperazine-2,3-dione. 1H NMR (CDCl3) δ 7.26 (m, 3H), 7.17 (m, 2H), 4.25 (A of AB, 1H, J=15.9 Hz), 4.20 (B of AB, 1H, J=15.6 Hz), 3.74 (m, 1H), 3.62 (m, 3H), 3.47 (m, 3H), 3.08 (m, 1H), 1.57 (m, 2H), 1.46 (s, 9H), 1.40 (s, 3H), 1.36 (m, 2H), 0.94 (t, 3H, J=7.2 Hz).

Workup

  1. washwashed with water and brine
  2. customDrying
  3. customsolvent evaporation and flash chromatography (silica gel, 0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f218d8881d8c4754a4dc73ee0a79a28c
Source dataset
uspto-grants-2010_10
Patent number
US07820674B2

Reaction notes

Loading…