Acetic Acid → Racemic 3-{4-[1-(4'-isopropyl-2-morpholin-4-ylmethyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid

HRID 1914335Notes

Reaction equation

HRID 1914335 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH:10]([C:15]2[CH:28]=[CH:27][C:18]([C:19]([NH:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:20])=[CH:17][CH:16]=2)[CH2:11][CH:12]([CH3:14])[CH3:13])[CH:6]=[CH:5][C:4]=1[C:29]1[CH:34]=[CH:33][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:31][CH:30]=1)=O.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>ClCCl.C(OCC)(=O)C>[CH:35]([C:32]1[CH:31]=[CH:30][C:29]([C:4]2[CH:5]=[CH:6][C:7]([O:9][CH:10]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([NH:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:20])=[CH:27][CH:28]=3)[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:8][C:3]=2[CH2:1][N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[CH:34][CH:33]=1)([CH3:36])[CH3:37]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 595181533-{4-[1-(2-Formyl-4'-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid

Product 1

HCID 59518154Racemic 3-{4-[1-(4'-isopropyl-2-morpholin-4-ylmethyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acidYield 29.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 3-{4-[1-(2-formyl-4′-isopropyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-propionic acid (240 mg, 0.48 mmol) and Morpholine (84 mg, 0.96 mmol) in dichloromethane (20 ml) is added NaBH(OAc)3 (143 mg, 0.67 mmol) and acetic acid (58 mg, 0.96 mmol). The resulting mixture is stirred overnight, diluted with ethyl actate, washed with 1N HCl, water, brine, dried over MgSO4, and concentrated. The residue is purified by column chromatography to afford 80 mg of the titled compound as a white solid. MS (ES): 573.5 [M+H]+.

Workup

  1. washwashed with 1N HCl, water, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-fc7950fdf8094e5491fcfbe118f915fe
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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