Sodium Hydroxide → HCID 22100281, compound

HRID 1457550Notes

Reaction equation

C([O:3][C:4]([CH:6]1[N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:9][N:8]([CH2:19][CH2:20][CH2:21][C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([N:31]4[CH:35]=[N:34][N:33]=[CH:32]4)[CH:29]=3)[NH:24][CH:23]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+]>CCO>[C:15]([O:14][C:12]([N:11]1[CH2:10][CH2:9][N:8]([CH2:19][CH2:20][CH2:21][C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([N:31]4[CH:32]=[N:33][N:34]=[CH:35]4)[CH:29]=3)[NH:24][CH:23]=2)[CH2:7][CH:6]1[C:4]([OH:5])=[O:3])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-tert-butyloxycarbonyl-1-[3-(5-(1,2,4-triazol-4-yl) -1H-indol-3-yl)propyl]piperazine-3-carboxylic acid ethyl ester contaminated with a small amount of the 2-isomer (524 mg, 1.1 mmol; see Example 3, Step 2) in EtOH (10 mL) was added NaOH (0.54 mL of a 4M aqueous solution, 2.2 mmol). The mixture was heated at 50° C. for 2 h, then cooled to room temperature and evaporated lit vacuo. The residue was dissolved in water (10 mL) and neutralized using 1M hydrochloric acid. The solvent was evaporated and the residue chromatographed on silica gel, eluting with CH2Cl2 :MeOH:AcOH (90:10:1→80:20:2), to afford 4-tert-butyloxycarbonyl -1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]piperazine-3-carboxylic acid, as a cream-coloured foam, contaminated with a small amount of the 2-isomer.

Workup

temperaturecooled to room temperature
customevaporated
dissolutionThe residue was dissolved in water (10 mL)
customThe solvent was evaporated
customthe residue chromatographed on silica gel
washeluting with CH2Cl2 :MeOH:AcOH (90:10:1→80:20:2)

Sources & evidence

ORD record: ord-82a91161c44f453c99931d7bc71c9288
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849746

Reaction notes

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