Ethyl bromoacetate → HCID 9955255, compound

HRID 1584576Notes

Reaction equation

HRID 1584576 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1[C:10]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:4].[H-].[Na+].Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C)C=O>[CH2:35]([O:34][C:32]([CH2:31][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([C:19]([OH:21])=[O:20])[CH:14]=2)[C:10]([C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[C:3]([O:2][CH3:1])=[O:4])=[C:11]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:33])[CH3:36]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 15434608HCID 15434608, compound

Product 1

HCID 9955255HCID 9955255, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-(2-methoxycarbonyl-cyclopent-1-enyl)-2-phenyl-1H-indole-6-carboxylic acid on Wang resin (100 mg; compound 7-3, prepared according to the is procedure outlined in Example 7) in dimethylformamide (1.5 mL) was added sodium hydride (60% in mineral oil; 20 mg) and the mixture was stirred at room temperature for 30 min. Ethyl bromoacetate (0.1 mL) was added and the mixture was stirred for 3 h. The mixture was filtered, washed with water (1×1.5 mL), tetrahydrofuran (2×1.5 mL), dichloromethane (2×1.5 mL), and dried. The product was cleaved from the resin by treatment with 1:1 trifluoroacetic acid/dichloromethane for 1 h; 1H NMR (DMSO-d6) δ 1.13 (t, J=7.1 Hz, 3 H), 1.80 (m, 2 H), 2.50 (m, 2 H), 2.63 (m, 2 H), 3.33 (s, 3 H), 4.09 (q, J=7.1 Hz, 7.30 (m, 2 H), 7.39 (d, J=8.5 Hz, 1 H), 7.48 (m, 3 H), 7.71 (d, J=7.2 Hz, 1 H), 8.11 (s, 1 H).

Workup

  1. stirringthe mixture was stirred for 3 h
  2. filtrationThe mixture was filtered
  3. washwashed with water (1×1.5 mL), tetrahydrofuran (2×1.5 mL), dichloromethane (2×1.5 mL)
  4. customdried
  5. waitThe product was cleaved from the resin by treatment with 1:1 trifluoroacetic acid/dichloromethane for 1 h

Sources & evidence

ORD record
ord-7c410dfc9fd3456f8ff002dddcd69319
Source dataset
uspto-grants-1999_08
Patent number
US05932743

Reaction notes

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