Diisopropylethylamine → HCID 67360202, compound

HRID 1667148Notes

Reaction equation

HRID 1667148 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]([OH:23])=O.[C:24]1([CH:30]2[O:35][CH2:34][CH2:33][NH:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C>ClCCl>[O:23]=[C:21]([N:32]1[CH2:33][CH2:34][O:35][CH:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:31]1)[CH2:20][N:3]1[CH2:4][CH2:5][CH2:6][C:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 911012-PhenylmorpholineHCID 673592802-(2-Oxo-3,3-diphenylpiperidin-1-yl)acetic acid

Product 1

HCID 67360202HCID 67360202, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E, 0.103 g, 0.334 mmol), 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.155 g, 0.408 mmol) and 2-phenylmorpholine (0.074 g, 0.371 mmol) in dichloromethane (0.5 mL) was added diisopropylethylamine (0.097 mL, 0.556 mmol), and the reaction mixture was stirred at room temperature. After stirring overnight, the reaction was directly loaded onto a silica gel column (Analogix®, SF15-12), and the product was eluted with a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes with a flow rate of 30 mL/minute. The product eluted with a more polar impurity. The product was rechromatographed over silica gel (Analogix®, SF15-12), and the title compound was eluted with a gradient of 0.4% to 7.5% methanol/dichloromethane over 20 minutes with a flow rate of 30 mL/minute. 1H NMR (300 MHz, CDCl3) δ ppm 7.18-7.40 (m, 15H), 4.37-4.68 (m, 3H), 3.98-4.17 (m, 2H), 3.32-3.85 (m, 6H), 2.64-2.70 (m, 2H), 1.82-1.88 (m, 2H); MS (ESI+) m/z 455 (M+H)+.

Workup

  1. stirringAfter stirring overnight
  2. washthe product was eluted with a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes with a flow rate of 30 mL/minute
  3. washThe product eluted with a more polar impurity
  4. customThe product was rechromatographed over silica gel (Analogix®, SF15-12)
  5. washthe title compound was eluted with a gradient of 0.4% to 7.5% methanol/dichloromethane over 20 minutes with a flow rate of 30 mL/minute

Sources & evidence

ORD record
ord-05bb1a3c372c4013a56d099538ed6118
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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