Sodium Hydroxide → HCID 59180183, compound

HRID 601935Notes

Reaction equation

[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]2[C:12]3[NH:13][C:14]([C:16]([O:18]CC)=[O:17])=[CH:15][C:11]=3[CH2:10][CH:9]=2)=[CH:3][CH:2]=1.[OH-].[Na+]>>[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:2]=[CH:3][C:4]([CH2:7][CH:8]2[C:12]3[NH:13][C:14]([C:16]([OH:18])=[O:17])=[CH:15][C:11]=3[CH2:10][CH2:9]2)=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 66874172HCID 66874172, compound

Product 1

HCID 59180183HCID 59180183, compoundYield 50%

Procedure

The title compound was synthesized from ethyl 6-(biphenyl-4-ylmethyl)-1,4-dihydrocyclopenta[b]pyrrole-2-carboxylate (0.0343 g, 0.1 mmol, 1 equiv) and sodium hydroxide (0.36 mL, 3.6 mmol, 10 M, 35 equiv), according to General Procedure 7. The resulting product was purified by preparative HPLC using the Chromeleon purification system. A 0.1% formic acid/1% acetonitrile mixture in water (aqueous phase) and methanol (no modifier added—organic phase) using a 50 mm Dynamax HPLC C-18 column at 28 mL/min (initial gradient of 70% methanol and increasing to 100% over 7 minutes) afforded the title compound (15.7 mg, 50%) with purity by HPLC of 93.3% (UV). LCMS m/e 316.2 (M−H). 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.08-2.20 (m, 1H) 2.41-2.50 (m, 2H) 2.75 (dd, J=13.62, 8.54 Hz, 1H) 3.06-3.12 (m, 1H) 6.55 (s, 1H) 7.24 (d, J=8.10 Hz, 2H) 7.28-7.33 (m, 1H) 7.41 (t, J=7.61 Hz, 2H) 7.53 (d, J=8.13 Hz, 2H) 7.60 (d, J=7.20 Hz, 2H) 8.50 (s, 1H).

Workup

customThe resulting product was purified by preparative HPLC
customthe Chromeleon purification system
temperatureincreasing to 100% over 7 minutes)

Sources & evidence

ORD record: ord-c94bcf11da3a40fcba2e6619d83ba83c
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902252B2

Reaction notes

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