Sodium Hydroxide → HCID 59432350, compound

HRID 507184Notes

Reaction equation

HRID 507184 reaction equation
C[O:2][C:3](=[O:50])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:17][CH2:16][CH2:15][C@H:14]([N:18]([CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=3)[C:19]3[N:20]=[N:21][N:22]([CH3:24])[N:23]=3)[C:13]3[CH:40]=[C:41]([CH3:49])[C:42]([C:45]([F:48])([F:47])[F:46])=[C:43]([CH3:44])[C:12]2=3)=[CH:6][CH:5]=1.[OH-].[Na+]>CO.O.Cl>[F:34][C:32]([F:33])([F:35])[C:30]1[CH:31]=[C:26]([CH:27]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:29]=1)[CH2:25][N:18]([C:19]1[N:20]=[N:21][N:22]([CH3:24])[N:23]=1)[C@H:14]1[CH2:15][CH2:16][CH2:17][N:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:50])=[O:2])=[CH:5][CH:6]=2)[C:12]2[C:43]([CH3:44])=[C:42]([C:45]([F:46])([F:47])[F:48])[C:41]([CH3:49])=[CH:40][C:13]1=2

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59432368HCID 59432368, compound

Product 1

HCID 59432350HCID 59432350, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 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]-7,9-dimethyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepin-1-ylmethyl}-benzoic 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% methanol in EtOAc) to afford the title compound. MS (ES+): 701 (M+H).

Workup

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

Sources & evidence

ORD record
ord-ffa769364f6a4ead863fe6a5315ef8dd
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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