Triphenylphosphine → (2S)-2-(2-borono-4-chlorophenoxy)-propanoic acid

HRID 1023790

반응식

HRID 1023790 반응식
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([B:23]2[O:27]C(C)(C)C(C)(C)[O:24]2)[CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:51]([O:56]C(C)(C)C)(=[O:55])[C@@H:52]([CH3:54])O>C1COCC1>[B:23]([C:18]1[CH:17]=[C:16]([Cl:15])[CH:21]=[CH:20][C:19]=1[O:22][C@@H:52]([CH3:54])[C:51]([OH:56])=[O:55])([OH:24])[OH:27]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 10953655tert-butyl (2R)-2-hydroxypropanoateHCID 672770614-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

생성물 1

HCID 67277298(2S)-2-(2-borono-4-chlorophenoxy)-propanoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

DIAD (3 ml) was added to a mixture of the product from step b) (3.51 g), triphenyl phosphine (3.98 g), tert-butyl (R)-(+) lactate (2.02 g) and THF (80 ml) at 0° C. overnight. The mixture was concentrated in vacuo. The residue was purified by flash column chromatography eluting with isohexane:ethyl acetate (7:3) to give the sub-title compound (4 g). The intermediate obtained was dissolved in acetone and 1M HCl (15 ml) was added, stirred for 20 min, then concentrated in vacuo. Redissolved in dichloromethane (10 ml) and added TFA (5 ml). Stirred for 2 h, then added water (1 ml), stirred for 1 h. The reaction mixture was then diluted (water) and made alkaline by adding dilute NaOH. The organic layer was separated and discarded. The aqueous phase was acidified with concentrated HCl to pH1, then washed with dichloromethane (×2). These organic extracts were dried (MgSO4) then concentrated in vacuo to give the sub-title compound. Yield 1.4 g

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by flash column chromatography
  3. washeluting with isohexane:ethyl acetate (7:3)

출처 및 근거

ORD 기록
ord-f920f5bd35ad4c8e8fcbfeb32daacd9c
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722741B2

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