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

HRID 1914333노트

반응식

HRID 1914333 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

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]−.

후처리

  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

출처 및 근거

ORD 기록
ord-ca238a98419d4d94b575bf30e2cb1e37
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609892B2

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