Sodium borohydride → Methyl N-{(4-bromophenyl)[4-(methylsulfonyl)phenyl]methyl}-L-leucinate

HRID 1620901노트

반응식

HRID 1620901 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[N:9][C@H:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.BrC1C=CC(C(C2C=CC(S(C)(=O)=O)=CC=2)=O)=CC=1.[BH4-].[Na+]>C(O)(=O)C.CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][CH:24]=2)[NH:9][C@H:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH:12]([CH3:13])[CH3:14])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 4311764Sodium borohydrideHCID 21262853(4-Bromophenyl)(4-(methylsulfonyl)phenyl)methanoneHCID 86590539methyl N-{(4-bromophenyl)[4-(methylsulfonyl)phenyl]methylene}leucinate

생성물 1

HCID 67298353Methyl N-{(4-bromophenyl)[4-(methylsulfonyl)phenyl]methyl}-L-leucinate

시약·촉매·용매 1

HCID 10129899Acetic acid methanol용매

실험 절차

To a solution of a 1:1 mixture of methyl N-{(4-bromophenyl)[4-(methylsulfonyl)phenyl]methylene}leucinate and (4-bromophenyl)[4-(methylsulfonyl)phenyl]methanone from step 1 (185 mg, −0.2 mmol) in acetic acid/methanol (1:3, 4 mL) was added sodium borohydride (˜400 mg) by portions every 30 min over 2 days (addition was stopped during the night) using a solid addition funnel. The reaction mixture was partitioned between EtOAc and water, the organic layer was dried over Na2SO4 and concentrated. The resulting mixture was purified by chromatography using EtOAc and hexane as eluant. Methyl N-{(4-bromophenyl)[4-(methylsulfonyl)phenyl]methyl}-L-leucinate was obtained as a colorless gum and (4-bromophenyl) [4-(methylsulfonyl)phenyl]methanol was obtained as a white solid.

후처리

  1. additionaddition
  2. additiona solid addition funnel
  3. customThe reaction mixture was partitioned between EtOAc and water
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting mixture was purified by chromatography

출처 및 근거

ORD 기록
ord-599b193bac044ff08be53eeeed962032
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772336B2

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