Sodium Hydroxide → HCID 59432369, compound

HRID 507183Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (S)-(4-{5-[(3-Chloro-5-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-7,9-dimethyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepin-1-ylmethyl}-cyclohexyl)-acetic acid methyl ester (0.1 mmol) in methanol (1 mL), add 4N sodium hydroxide (0.5 mL). Heat the mixture at 60° C. for 3 h. Dilute the cooled mixture with water and 1N HCl to bring the pH to 6-7 and extract with CH2Cl2 (3×15 mL). Combine the organic layers, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by chromatography (elution with 5%-10% methanol in EtOAc) to afford the title compound. MS (ES+): 687 (M+H).

Workup

extractionextract with CH2Cl2 (3×15 mL)
dry with materialCombine the organic layers, dry over sodium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
customto give a residue
customPurify the residue
washby chromatography (elution with 5%-10% methanol in EtOAc)

Sources & evidence

ORD record: ord-e1e98a4a52ab4f33aa08f3e275223d34
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786108B2

Reaction notes

Loading…