Reaktion #8933

ord-38a2481c78754a3cb5c7d1ecd2475eae

Reaktionsgleichung

O=S(=O)([O-])O.[K+]
KHSO4
COC(=O)[C@@H](C)CS(=O)(=O)N(Cc1ccccc1)C(c1ccccc1)c1ccccc1
methyl 3-[N-(benzyl)-N-(diphenylmethyl)aminosulfonyl]-2(R)-methylpropionate
[Li+].[OH-]
LiOH
CO
MeOH
→
C[C@@H](CS(=O)(=O)N(Cc1ccccc1)C(c1ccccc1)c1ccccc1)C(=O)O
3-[N-(benzyl)-N-(diphenylmethyl)aminosulfonyl]-2(R)-methylpropionic acid
Ausbeute 80.7%

Edukte

O=S(=O)([O-])O.[K+]
KHSO4
COC(=O)[C@@H](C)CS(=O)(=O)N(Cc1ccccc1)C(c1ccccc1)c1ccccc1
methyl 3-[N-(benzyl)-N-(diphenylmethyl)aminosulfonyl]-2(R)-methylpropionate
[Li+].[OH-]
LiOH
CO
MeOH

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
ethyl acetate
C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeA 50 mL round bottom flask equipped with magnetic stir bar
  2. 2
    Sonstigeto get homogeneous solution
  3. 3
    WaschenThe organic phase was washed with brine
  4. 4
    Sonstigedried
  5. 5
    Einengenconcentrated in vacuo

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07091219B2uspto-grants-2006_08