Sodium Hydroxide → HCID 11585691, compound

HRID 507129Notes

Reaction equation

HRID 507129 reaction equation
C([O:3][C:4](=[O:51])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][N:13]2[CH2:19][CH2:18][CH2:17][C@H:16]([N:20]([CH2:27][C:28]3[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[C:30]([C:38]([F:41])([F:40])[F:39])[CH:29]=3)[C:21]3[N:22]=[N:23][N:24]([CH3:26])[N:25]=3)[C:15]3[CH:42]=[C:43]([CH3:50])[C:44]([C:46]([F:49])([F:48])[F:47])=[CH:45][C:14]2=3)[CH2:8][CH2:7]1)C.[OH-].[Na+]>CO.O>[F:37][C:34]([F:35])([F:36])[C:32]1[CH:33]=[C:28]([CH:29]=[C:30]([C:38]([F:39])([F:40])[F:41])[CH:31]=1)[CH2:27][N:20]([C:21]1[N:22]=[N:23][N:24]([CH3:26])[N:25]=1)[C@H:16]1[CH2:17][CH2:18][CH2:19][N:13]([CH2:12][CH:9]2[CH2:10][CH2:11][N:6]([CH2:5][C:4]([OH:51])=[O:3])[CH2:7][CH2:8]2)[C:14]2[CH:45]=[C:44]([C:46]([F:47])([F:48])[F:49])[C:43]([CH3:50])=[CH:42][C:15]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11549451HCID 11549451, compound

Product 1

HCID 11585691HCID 11585691, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-(4-{5-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepin-1-ylmethyl}-piperidin-1-yl)-acetic acid ethyl ester (0.11 mmol) in methanol (5 mL), add 5.0 N sodium hydroxide (2 mL). After heating at 60° C. for 6 h cool to room temperature and dilute with water (20 mL). Extract the organics with ethyl acetate (3×10 mL). Dry the combined organic phases over sodium sulfate, filter, and remove solvent under vacuum, to afford the title compound as a colorless foam. MS (ES+): 708 (M+H).

Workup

  1. temperaturecool to room temperature
  2. extractionExtract the organics with ethyl acetate (3×10 mL)
  3. dry with materialDry the combined organic phases over sodium sulfate
  4. filtrationfilter
  5. customremove solvent under vacuum

Sources & evidence

ORD record
ord-608daf50be8c439e9802e4fb551ed167
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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