Lithium hydroxide, monohydrate → 3-(Tert-butoxycarbonylamino)-2-(4-chloro-3-fluorobenzyl)propanoic acid

HRID 1675839노트

반응식

HRID 1675839 반응식
O[Li].O.[C:4]([O:8][C:9]([NH:11][CH2:12][CH:13]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([F:27])[CH:21]=1)[C:14]([O:16]CC)=[O:15])=[O:10])([CH3:7])([CH3:6])[CH3:5]>O.C1COCC1.CO>[C:4]([O:8][C:9]([NH:11][CH2:12][CH:13]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([F:27])[CH:21]=1)[C:14]([OH:16])=[O:15])=[O:10])([CH3:7])([CH3:5])[CH3:6]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 67338495Ethyl 3-(tert-butoxycarbonylamino)-2-(4-chloro-3-fluorobenzyl)propanoate

생성물 1

HCID 673397543-(Tert-butoxycarbonylamino)-2-(4-chloro-3-fluorobenzyl)propanoic acid수율 100.5%

시약·촉매·용매 2

HCID 962Water용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

A solution of Boc2O (1.3 g, 6.1 mmol) and ethyl 3-amino-2-(4-chloro-3-fluorobenzyl)propanoate (1.6 g, 6.1 mmol) in DCM (10 mL) was stirred overnight. The mixture was concentrated in vacuo and chromatographed (SiO2) using DCM as eluent to give ethyl 3-(tert-butoxycarbonylamino)-2-(4-chloro-3-fluorobenzyl)propanoate. LiOH—H2O (0.26 g, 6.1 mmol) in H2O (7 mL) was added to a solution of ethyl 3-(tert-butoxycarbonylamino)-2-(4-chloro-3-fluorobenzyl)propanoate (0.55 g, 1.5 mmol) in THF/MeOH (7/7 mL) and stirred overnight. The mixture was concentrated in vacuo, acidifed to a pH of 1 with 1.0N HCl, and extracted with DCM. The DCM extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was chromatographed (SiO2) using 10% MeOH/DCM as eluent to give 3-(tert-butoxycarbonylamino)-2-(4-chloro-3-fluorobenzyl)propanoic acid (0.5 g). LCMS (APCI+) [M−Boc+H]+ 232.0; Rf: 2.09 min.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with DCM
  3. dry with materialThe DCM extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was chromatographed (SiO2)

출처 및 근거

ORD 기록
ord-0ed5578d7ca44345b0cee016db1988c0
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003651B2

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