Hydrochloric Acid → (S)-5-{9-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino)-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]inden-5-yl)-3,3-dimethyl-pentanoic acid

HRID 507100Notes

Reaction equation

HRID 507100 reaction equation
C[O:2][C:3](=[O:46])[CH2:4][C:5]([CH3:45])([CH3:44])[CH2:6][CH2:7][N:8]1[C:21]2[C:13](=[CH:14][C:15]3[CH2:16][O:17][CH2:18][C:19]=3[CH:20]=2)[C@@H:12]([N:22]([CH2:29][C:30]2[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=2)[C:23]2[N:24]=[N:25][N:26]([CH3:28])[N:27]=2)[CH2:11][CH2:10][CH2:9]1.[OH-].[Na+].Cl>CO.O>[F:39][C:36]([F:37])([F:38])[C:34]1[CH:35]=[C:30]([CH:31]=[C:32]([C:40]([F:41])([F:42])[F:43])[CH:33]=1)[CH2:29][N:22]([C:23]1[N:24]=[N:25][N:26]([CH3:28])[N:27]=1)[C@@H:12]1[C:13]2=[CH:14][C:15]3[CH2:16][O:17][CH2:18][C:19]=3[CH:20]=[C:21]2[N:8]([CH2:7][CH2:6][C:5]([CH3:45])([CH3:44])[CH2:4][C:3]([OH:46])=[O:2])[CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59432400(S)-5-(9-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]inden-5-yl)-3,3-dimethyl-pentanoic acid methyl ester

Product 1

HCID 11721545(S)-5-{9-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino)-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]inden-5-yl)-3,3-dimethyl-pentanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-5-{9-[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]inden-5-yl}-3,3-dimethyl-pentanoic acid methyl ester (0.113 mmol) in methanol (3 mL), add 5 N NaOH (2 mL) and heat to 60° C. After stirring for 6 h, cool the reaction to room temperature, dilute with water (10 mL) and neutralize with 5 M HCl. Extract the organics with ethyl acetate (2×20 mL). Combine the organic portions, dry over sodium sulfate, filter, and remove the solvent under vacuum. Chromatograph the product over silica gel, eluting with ethyl acetate/hexane (20-60%) to afford the title compound as a colorless foam. MS (ES+): 641.3 (M+H).

Workup

  1. temperaturecool
  2. customthe reaction to room temperature
  3. extractionExtract the organics with ethyl acetate (2×20 mL)
  4. dry with materialCombine the organic portions, dry over sodium sulfate
  5. filtrationfilter
  6. customremove the solvent under vacuum
  7. washChromatograph the product over silica gel, eluting with ethyl acetate/hexane (20-60%)

Sources & evidence

ORD record
ord-6d18f43b3cd0413b88f6abee065c49c1
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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