Hydrochloric Acid → HCID 57771502, compound

HRID 2070579Notes

Reaction equation

HRID 2070579 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH:5]([C:25]1[N:29]([CH3:30])[N:28]=[N:27][N:26]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][C:16]3([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:15]2)=[CH:8][CH:7]=1.O1CCCC1.[OH-].[Na+].Cl>O.CO>[CH3:30][N:29]1[C:25]([CH:5]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]3[CH2:19][CH2:18][CH2:17][C:16]4([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[CH2:15]3)=[CH:8][CH:7]=2)[CH2:4][C:3]([OH:31])=[O:2])=[N:26][N:27]=[N:28]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57771627HCID 57771627, compound

Product 1

HCID 57771502HCID 57771502, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(1-methyl-1H-tetrazol-5-yl)-3-[4-(spiro[5.5]undec-2-ylmethoxy)-phenyl]-propionic acid methyl ester (41 mg) obtained in Step 8 in a mixed solvent of tetrahydrofuran (1 mL)-methanol (0.5 mL)-water (0.5 mL) was added 2N aqueous sodium hydroxide solution (0.144 mL), followed by stirring the reaction mixture at room temperature for 18 hours. Then, after addition of 1N aqueous hydrochloric acid solution (0.3 mL), the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by thin-layer column chromatography on silica gel (acetic acid:ethyl acetate:chloroform (volume ratio)=0.1:1:10) to give 3-(1-methyl-1H-tetrazol-5-yl)-3-[4-(spiro[5.5]undec-2-ylmethoxy)-phenyl]-propionic acid (39 mg) as the desired compound.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by thin-layer column chromatography on silica gel (acetic acid:ethyl acetate:chloroform (volume ratio)=0.1:1:10)

Sources & evidence

ORD record
ord-e4a2ac2a07e049b0a3d8e7cd81440681
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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