Ethyl Acetate → HCID 59495659, compound

HRID 219964Notes

Reaction equation

HRID 219964 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([C:17]2[N:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH3:34])=[C:24]([CH2:35][O:36][CH3:37])[CH:23]=3)[O:19][N:18]=2)[CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]([O:11]C)=[O:10])=[O:5].[OH-].[Na+].CCOC(C)=O>CO.O>[F:1][C:2]1[CH:16]=[C:15]([C:17]2[N:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH3:34])=[C:24]([CH2:35][O:36][CH3:37])[CH:23]=3)[O:19][N:18]=2)[CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[O:5]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 59495746HCID 59495746, compound

Product 1

HCID 59495659HCID 59495659, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of example 117 (1 860 mg; 3.69 mmol) in MeOH (40 mL), sodium hydroxide (3.69 mL; 5 M; 18.5 mmol) in H2O was added. The reaction was stirred at RT for 1 h. EtOAc was added and the organic phase washed 3 times with HCl 1M. The organic phase was dried over MgSO4, filtered off and concentrated to afford the title compound as a white powder (1490.0 mg, 82%). 1H NMR: (DMSO-d6, 300 MHz) δ 8.58 (m, 1H), 8.33 (brs, 1H), 8.18 (dd, J=1.7 Hz, 8 Hz, 1H), 8.03 (dd, J=1.7 Hz, 8 Hz, 1H), 7.95 (d, J=10.6 Hz, 1H), 7.84 (t, J=7.6 Hz, 1H), 7.44 (d, J=7.9 Hz, 1H), 7.40-7.22 (m, 3H), 7.15 (m, 1H), 4.23 (d, J=12.9 Hz, 1H), 4.17 (d, J=12.9 Hz, 1H), 3.49 (m, 2H), 3.25 (s, 3H), 2.53 (m, 2H), 2.04 (s, 3H). LC/MS (Method B): 490.3 (M+H)+ 488.4 (M−H)−. HPLC (Method A) Rt: 4.83 min (purity: 99.7%).

Workup

  1. washthe organic phase washed 3 times with HCl 1M
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered off
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3e869af10e5c4c8495b361623cf85921
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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