Diisopropylethylamine → HCID 67443748, compound

HRID 1667163Notes

Reaction equation

HRID 1667163 reaction equation
[O:1]=[C:2]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:20][C:21](O)=[O:22].[NH:24]1[CH2:29][CH2:28][CH:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:26][CH2:25]1.C(N(C(C)C)CC)(C)C>ClCCl>[O:1]=[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:20][C:21]([N:24]1[CH2:25][CH2:26][CH:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:36])[CH3:35])[CH2:28][CH2:29]1)=[O:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 673592802-(2-Oxo-3,3-diphenylpiperidin-1-yl)acetic acid

Product 1

HCID 67443748HCID 67443748, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E, 0.31 g, 1 mmol), tert-butyl piperidin-4-ylcarbamate (CAS 73874-95-0, 0.2 g, 1 mmol) and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.38 g, 1 mmol) in dichloromethane (10 mL) was added diisopropylethylamine (0.7 mL), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then diluted with dichloromethane and washed with sequentially with 20 mL of 1 N HCl, water, 20 ml, of 1 N NaOH, and water. The organic phase was dried over magnesium sulfate and concentrated in vacuo to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.33 (m, 8H), 7.21 (m, 2H), 4.45 (m, 2H), 4.03 (m, 1H), 3.77 (m, 1H), 3.49 (m, 2H), 3.11 (m, 1H), 2.79 (m, 1H), 2.63 (m, 2H), 1.97 (m, 2H), 1.83 (m, 2H), 1.45 (m, 9H), 1.32 (m, 2H).

Workup

  1. washwashed with sequentially with 20 mL of 1 N HCl, water, 20 ml
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-736be6965023455ba55a1d56a28d8f16
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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