Acetic Acid → HCID 11661699, compound

HRID 2056010Notes

Reaction equation

C[O:2][C:3]([C:5]1([NH:9][C:10]([C:12]2[CH:20]=[C:19]3[C:15]([C:16]([CH:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)=[C:17]([Br:22])[N:18]3[CH3:21])=[CH:14][CH:13]=2)=[O:11])[CH2:8][CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].C(O)(=O)C>C(O)CC.O>[Br:22][C:17]1[N:18]([CH3:21])[C:19]2[C:15]([C:16]=1[CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)=[CH:14][CH:13]=[C:12]([C:10]([NH:9][C:5]1([C:3]([OH:4])=[O:2])[CH2:8][CH2:7][CH2:6]1)=[O:11])[CH:20]=2

Participants

Conditions

Temperature: 89 °C

Procedure

To a suspension of 1-[(2-bromo-3-cyclopentyl-1-methyl-1H-indole-6-carbonyl)-amino]-cyclobutanecarboxylic acid methyl ester (20.00 g, 46.15 mmol) in n-propanol (100 mL) and water (100 mL) was added 50% NaOH (4.06 g, 50.77 mmol). The mixture was heated at 89° C. until no starting material was left (0.5 h). The clear solution was cooled to 50° C. and acetic acid (4.23 mL, 73.85 mmol) was added dropwise to adjust the pH to 5-6. The product was precipitated as a white solid. The suspension was brought to reflux for 0.5 h and then allowed to cool to room temperature in no less than 1 h. The solid was collected by filtration, washed by 1:1 water/n-propanol (100 mL) and water (200 mL). The 1-[(2-bromo-3-cyclopentyl-1-methyl-1H-indole-6-carbonyl)-amino}-cyclobutanecarboxylic acid, obtained as a white solid was dried under vacuum until constant weight (17.78 g, 97%).

Workup

temperatureThe clear solution was cooled to 50° C.
customThe product was precipitated as a white solid
temperatureto reflux for 0.5 h
temperatureto cool to room temperature in no less than 1 h
filtrationThe solid was collected by filtration
washwashed by 1:1 water/n-propanol (100 mL) and water (200 mL)

Sources & evidence

ORD record: ord-5825d05e8c214e6a869879bf839cbdf8
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332614B2

Reaction notes

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