Sodium borohydride → 3-{4-[1-(2-Hydroxymethyl-4'-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid

HRID 1914333Notes

Reaction equation

HRID 1914333 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][CH2:5][NH:6][C:7](=[O:37])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=3)=[C:22]([CH:35]=[O:36])[CH:21]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1.[BH4-].[Na+]>CO.C(OCC)(=O)C>[OH:36][CH2:35][C:22]1[CH:21]=[C:20]([O:19][CH:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:38])=[O:2])=[O:37])=[CH:9][CH:10]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])[CH:25]=[CH:24][C:23]=1[C:26]1[CH:27]=[CH:28][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866159863-{4-[1-(2-Formyl-4'-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester

Product 1

HCID 595181863-{4-[1-(2-Hydroxymethyl-4'-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acidYield 263.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 3-{4-[1-(2-formyl-4′-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester (36 mg, 0.07 mmol) in methanol (5 ml) is added NaBH4 (3 mg, 0.07 mmol). After 2 h, the mixture is diluted with ethyl actate, washed with 1N HCl, water, brine, dried over MgSO4, and concentrated. The residue is taken into methanol (20 mL), followed by the addition of sodium hydroxide (5 N aqueous, 1 mL), stirred for 4 h. The reaction mixture is concentrated and acidified by 5 N HCl (1 mL), extracted with ethyl acetate. Combined organic layers are washed with water and brine, dried over sodium sulfate. Concentration gives the title compound (93 mg) as a white solid. MS (ES): 502.2 [M−H]−.

Workup

  1. washwashed with 1N HCl, water, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. additionfollowed by the addition of sodium hydroxide (5 N aqueous, 1 mL)
  5. concentrationThe reaction mixture is concentrated
  6. extractionextracted with ethyl acetate
  7. washCombined organic layers are washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationConcentration

Sources & evidence

ORD record
ord-ca238a98419d4d94b575bf30e2cb1e37
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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