Hydrochloric Acid → HCID 59432316, compound

HRID 507175Notes

Reaction equation

HRID 507175 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]([N:14]2[CH2:20][CH2:19][CH2:18][C@H:17]([N:21]([CH2:28][C:29]3[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=3)[C:22]3[N:23]=[N:24][N:25]([CH3:27])[N:26]=3)[C:16]3[CH:43]=[C:44]([CH3:51])[C:45]([C:47]([F:50])([F:49])[F:48])=[CH:46][C:15]2=3)=[O:13])[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].Cl>CO.O>[C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]([N:14]2[CH2:20][CH2:19][CH2:18][C@H:17]([N:21]([CH2:28][C:29]3[CH:34]=[C:33]([C:35]([F:37])([F:36])[F:38])[CH:32]=[C:31]([C:39]([F:41])([F:40])[F:42])[CH:30]=3)[C:22]3[N:23]=[N:24][N:25]([CH3:27])[N:26]=3)[C:16]3[CH:43]=[C:44]([CH3:51])[C:45]([C:47]([F:50])([F:49])[F:48])=[CH:46][C:15]2=3)=[O:13])[CH2:7][CH2:6]1)([OH:4])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59432494HCID 59432494, compound

Product 1

HCID 59432316HCID 59432316, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-5-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid 4-methoxycarbonyl-cyclohexyl ester (0.14 mmol) in methanol (5 mL), add 5N sodium hydroxide (14 mmol). After heating the mixture at 60° C. for 2 h, cool to room temperature and dilute with water (20 mL). Neutralize the mixture using 5M HCl and extract the organics using ethyl actate (3×5 mL). Dry the combined organics over sodium sulfate, filter, and remove the solvent under vacuum. Chromatograph the crude product over silica gel, eluting with methanol/dichloromethane (0-5%) to obtain the separated cis and trans isomers. MS (ES+): 723 (M+H).

Workup

  1. temperaturecool to room temperature
  2. extractionextract the
  3. dry with materialDry the combined organics over sodium sulfate
  4. filtrationfilter
  5. customremove the solvent under vacuum
  6. washChromatograph the crude product over silica gel, eluting with methanol/dichloromethane (0-5%)
  7. customto obtain the separated cis and trans isomers

Sources & evidence

ORD record
ord-6d5b690b8fbf46358bccc57ca103c102
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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