Ethanol → HCID 11514561, compound

HRID 1430342Notes

Reaction equation

HRID 1430342 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH2:15][CH2:16][Cl:17])=[C:9]([O:18][CH3:19])[CH:8]=2)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].CCO>O>[Cl:17][CH2:16][CH2:15][O:14][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[O:18][CH3:19])[NH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:13]2

Participants

5

Reactant 3

HCID 702EthanolHCID 10796Cesium carbonateHCID 11680771HCID 11680771, compound

Product 1

HCID 11514561HCID 11514561, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of ester 17 (2.00 g, 7.05 mmol), Cs2CO3 (3.45 g, 10.6 mmol), 95% EtOH (40 mL), and water (20 mL) was heated at reflux for 8 h. After cooling to room temperature the solvent was removed in vacuo, the residue was treated with water (50 μL), and the resulting solution was acidified with 2 M HCl. The formed precipitate was isolated by filtration, washed with water (100 mL), and dried in vacuo to give 18 (1.80 g, 95%) as a beige solid. 1H NMR (300 MHz, DMSO-d6): δ=3.81 (s, 3 H, OMe), 3.93 (t, J=5.3 Hz, 2 H, 2′-H2), 4.21 (t, J=5.3 Hz, 2 H, 1′-H2), 6.91 (s, 1 H, 7-H), 6.96 (d, J=2.1 Hz, 1 H, 3-H), 7.15 (s, 1 H, 4-H), 11.44 (sbr, 1 H, NH), 12.57 (sbr, 1 H, CO2H) ppm; 13C NMR (50.3 MHz, DMSO-d6): δ=43.0 (C-2′), 55.6 (OMe), 69.5 (C-1′), 94.9 (C-7), 105.8 (C-4), 107.5 (C-3), 119.8 (C-3a), 126.8 (C-2), 133.0 (C-7a), 143.9 (C-5), 149.5 (C-6), 162.4 (C═O) ppm; MS (70 eV, EI): m/z (%)=269 (100) [M]+, 206 (58) [M-(CH2)2Cl]+; C12H12ClNO4 (269.68): calcd. C, 53.44; H, 4.49; found C, 53.54; H, 4.29.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. customwas removed in vacuo
  4. additionthe residue was treated with water (50 μL)
  5. customThe formed precipitate was isolated by filtration
  6. washwashed with water (100 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-06e6a90393a04092b1ddf418a7543515
Source dataset
uspto-grants-2015_01
Patent number
US08940784B2

Reaction notes

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