Hydrochloric Acid → HCID 72297340, compound

HRID 507172Notes

Reaction equation

HRID 507172 reaction equation
C[O:2][C:3](=[O:49])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][N:12]2[C:25]3[C:17](=[CH:18][C:19]4[CH2:20][O:21][CH2:22][C:23]=4[C:24]=3[CH3:26])[C@@H:16]([N:27]([CH2:34][C:35]3[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[C:37]([C:45]([F:48])([F:47])[F:46])[CH:36]=3)[C:28]3[N:29]=[N:30][N:31]([CH3:33])[N:32]=3)[CH2:15][CH2:14][CH2:13]2)[CH2:7][CH2:6]1.[OH-].[Na+].Cl>CO.O>[F:48][C:45]([F:46])([F:47])[C:37]1[CH:36]=[C:35]([CH:40]=[C:39]([C:41]([F:42])([F:43])[F:44])[CH:38]=1)[CH2:34][N:27]([C:28]1[N:29]=[N:30][N:31]([CH3:33])[N:32]=1)[CH:16]1[C:17]2=[CH:18][C:19]3[CH2:20][O:21][CH2:22][C:23]=3[C:24]([CH3:26])=[C:25]2[N:12]([CH2:11][CH:8]2[CH2:9][CH2:10][CH:5]([CH2:4][C:3]([OH:49])=[O:2])[CH2:6][CH2:7]2)[CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59432512HCID 59432512, compound

Product 1

HCID 72297340HCID 72297340, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-(4-{9-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-4-methyl-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]inden-5-ylmethyl}-cyclohexyl)-acetic acid methyl ester (0.15 mmol) in methanol (5 mL), add 5 N sodium hydroxide (3 mL). Heat the mixture to 60° C. for 2 h, then cool to room temperature and dilute with water (20 mL). Neutralize the reaction with 5M HCl and extract the organics with ethyl acetate (3×10 mL). Dry the combined organics over sodium sulfate, filter, and remove the solvent under vacuum. Chromatograph the product over silica gel, eluting with ethyl acetate/hexane (10-70%) to obtain the title compound as a colorless foam. MS (ES+): 681 (M+H).

Workup

  1. temperaturecool to room temperature
  2. extractionextract the organics with ethyl acetate (3×10 mL)
  3. dry with materialDry the combined organics over sodium sulfate
  4. filtrationfilter
  5. customremove the solvent under vacuum
  6. washChromatograph the product over silica gel, eluting with ethyl acetate/hexane (10-70%)

Sources & evidence

ORD record
ord-9d21363673414befa14c9c266394f3bb
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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