Methanol → 3-[N-(benzyl)-N-(diphenylmethyl)aminosulfonyl]-2(R)-methylpropionic acid

HRID 8837

반응식

HRID 8837 반응식
[CH2:1]([N:8]([CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[S:9]([CH2:12][C@H:13]([CH3:18])[C:14]([O:16]C)=[O:15])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].CO.OS([O-])(=O)=O.[K+]>C1COCC1.C(OCC)(=O)C>[CH2:1]([N:8]([CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[S:9]([CH2:12][C@H:13]([CH3:18])[C:14]([OH:16])=[O:15])(=[O:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 18738452methyl 3-[N-(benzyl)-N-(diphenylmethyl)aminosulfonyl]-2(R)-methylpropionate

생성물 1

HCID 187384373-[N-(benzyl)-N-(diphenylmethyl)aminosulfonyl]-2(R)-methylpropionic acid수율 80.7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A 50 mL round bottom flask equipped with magnetic stir bar was charged with 320 mg of methyl 3-[N-(benzyl)-N-(diphenylmethyl)aminosulfonyl]-2(R)-methylpropionate and 120 mg LiOH (4 eq) in 4 mL 50% aq THF. After 5 minutes 2 mL MeOH added to get homogeneous solution, after 1 hour the reaction was partioned between ethyl acetate and 5% aq KHSO4. The organic phase was washed with brine, dried, and concentrated in vacuo to yield 250 mg of 3-[N-(benzyl)-N-(diphenylmethyl)aminosulfonyl]-2(R)-methylpropionic acid as a clear semi-solid. HRMS (M+Li): calcd. 430.1664, obs. 430.1698.

후처리

  1. customA 50 mL round bottom flask equipped with magnetic stir bar
  2. customto get homogeneous solution
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-38a2481c78754a3cb5c7d1ecd2475eae
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091219B2

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