Ethanol → HCID 68416047, compound

HRID 659117Notes

Reaction equation

HRID 659117 reaction equation
C[O:2][C:3](=[O:26])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]([C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)=[O:14])[N:7]=1.CCO.[OH-].[Na+]>C1COCC1>[C:20]1([C:17]2[O:16][C:15]([C:13]([NH:12][C:8]3[N:7]=[C:6]([CH:5]=[CH:4][C:3]([OH:26])=[O:2])[CH:11]=[CH:10][CH:9]=3)=[O:14])=[CH:19][CH:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 68414910HCID 68414910, compound

Product 1

HCID 68416047HCID 68416047, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ester (39) (35 mg, 0.10 mmol) was hydrolysed using Method C, except that EtOH (2 mL), THF (1 mL) and 1 M NaOH (2 mL) were used, and the reaction was stirred for 2 hours. After work-up, the crude product was purified by preparative HPLC to give the title compound. Yield: 9.8 mg, 29%; LC-MS tr 2.00 min; HPLC Purity: 97%; MS (ES+) m/z 335 (M+H); 1H NMR (400 MHz; MeOH): δ 6.95 (d, 1H), 7.05 (d, 1H), 7.35-7.55 (m, 5H), 7.65 (d, 1H), 7.85-8.00 (m, 3H), 8.30 (d, 1H)

Workup

  1. customAfter work-up, the crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-342c7c33c79b4c57a0f635d10c4664ba
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

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