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

HRID 1160921ノート

反応式

HRID 1160921 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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 acetate, 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]+.

後処理

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

出典と根拠

ORDレコード
ord-0a1aeae19dbb4289a13c0c78603cdd0a
出典データセット
uspto-grants-2010_10
特許番号
US07816557B2

反応ノート

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