Hydrochloric Acid → HCID 11513028, compound

HRID 507106Notes

Reaction equation

[OH-].[Na+].C[O:4][C:5]([C:7]([CH3:49])([CH3:48])[CH2:8][O:9][C:10]([N:12]1[C:25]2[C:17](=[CH:18][C:19]3[CH2:20][CH2:21][CH2:22][C:23]=3[CH:24]=2)[C@@H:16]([N:26]([CH2:33][C:34]2[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[C:36]([C:44]([F:47])([F:46])[F:45])[CH:35]=2)[C:27]2[N:28]=[N:29][N:30]([CH3:32])[N:31]=2)[CH2:15][CH2:14][CH2:13]1)=[O:11])=[O:6].Cl.C(OCC)(=O)C>CO.O>[C:5]([C:7]([CH3:49])([CH3:48])[CH2:8][O:9][C:10]([N:12]1[C:25]2[C:17](=[CH:18][C:19]3[CH2:20][CH2:21][CH2:22][C:23]=3[CH:24]=2)[C@@H:16]([N:26]([CH2:33][C:34]2[CH:35]=[C:36]([C:44]([F:47])([F:45])[F:46])[CH:37]=[C:38]([C:40]([F:42])([F:43])[F:41])[CH:39]=2)[C:27]2[N:28]=[N:29][N:30]([CH3:32])[N:31]=2)[CH2:15][CH2:14][CH2:13]1)=[O:11])([OH:6])=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

Add aqueous 5 M NaOH (2.4 mL, 12 mmol) to a solution of (S)-9-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-2,3,6,7,8,9-hexahydro-1H-5-aza-cyclohepta[f]indene-5-carboxylic acid 2-methoxycarbonyl-2-methyl-propyl ester (86 mg, 0.13 mmol) in methanol (3.4 mL). Heat the mixture at 60° C. for 1 h. Cool down to room temperature. Dilute with water and neutralize with 2 M HCl. Extract aqueous phase with ethyl acetate. Dry organic layers with anhydrous sodium sulphate and evaporate the solvent. Purify the residue by chromatography (elution with dichloromethane/methanol) to afford the title compound (62 mg, 73%). MS (ES+): 655 (M+H).

Workup

temperatureCool down to room temperature
customDry organic layers with anhydrous sodium sulphate and evaporate the solvent
customPurify the residue
washby chromatography (elution with dichloromethane/methanol)

Sources & evidence

ORD record: ord-9d5b102efd204cabac2310a816008d20
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786108B2

Reaction notes

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