Sodium Hydroxide → HCID 59432404, compound

HRID 507179Notes

Reaction equation

HRID 507179 reaction equation
C[O:2][C:3](=[O:47])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][N:12]2[CH2:18][CH2:17][CH2:16][C@H:15]([N:19]([CH2:26][C:27]3[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([Cl:37])[CH:28]=3)[C:20]3[N:21]=[N:22][N:23]([CH3:25])[N:24]=3)[C:14]3[CH:38]=[C:39]([CH3:46])[C:40]([C:42]([F:45])([F:44])[F:43])=[CH:41][C:13]2=3)[CH2:7][CH2:6]1.[OH-].[Na+]>CO.O.Cl>[Cl:37][C:29]1[CH:28]=[C:27]([CH:32]=[C:31]([C:33]([F:36])([F:34])[F:35])[CH:30]=1)[CH2:26][N:19]([C:20]1[N:21]=[N:22][N:23]([CH3:25])[N:24]=1)[C@H:15]1[CH2:16][CH2:17][CH2:18][N:12]([CH2:11][CH:8]2[CH2:7][CH2:6][CH:5]([CH2:4][C:3]([OH:47])=[O:2])[CH2:10][CH2:9]2)[C:13]2[CH:41]=[C:40]([C:42]([F:43])([F:44])[F:45])[C:39]([CH3:46])=[CH:38][C:14]1=2

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59432340HCID 59432340, compound

Product 1

HCID 59432404HCID 59432404, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-(4-{5-[(3-Chloro-5-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepin-1-ylmethyl}-cyclohexyl)-acetic acid methyl ester (0.1 mmol) in methanol (1 mL), add 4N sodium hydroxide (0.4 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 and wash with water and brine, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by chromatography (elution with 5%-20% methanol in EtOAc) to afford the title compound. MS (ES+): 673 (M+H).

Workup

  1. extractionextract with CH2Cl2 (3×15 mL)
  2. washCombine the organic layers and wash with water and brine
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto give a residue
  7. customPurify the residue
  8. washby chromatography (elution with 5%-20% methanol in EtOAc)

Sources & evidence

ORD record
ord-19eca10157424f789fcff19c3fb12167
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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