Lithium Hydroxide → [4-(2-Boc-amino-ethyl)-phenyl]-acetic acid

HRID 484450노트

반응식

HRID 484450 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C)=[O:19])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 19747487HCID 19747487, 화합물

생성물 1

HCID 19747634[4-(2-Boc-amino-ethyl)-phenyl]-acetic acid수율 96.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 4-(tertiarybutyloxy carbonylaminoethyl)-phenylacetate (0.500 g, 1.71 mmol) in a mixture of tetrahydrofuran (20 ml) and water (10 ml) was added aqueous lithium hydroxide (3.8 ml of a 0.50M solution, 1.90 mmol) and the resulting mixture was stirred at room temperature for 16 h. The organic solvent was removed under vacuum and the residue was diluted with water (40 ml), acidified with concentrated hydrochloric acid and extracted with ethyl acetate (2×30 ml). The combined extracts were washed with brine (1×30 ml), dried (MgSO4) and evaporated to give the pure title compound as colourless crystals (0.460 g), m.p. 94°-95° C. δ (360 MHz, CDCl3) 1.42 (9H, s, C(CH3)3), 2.77 (2H, br, m, ArCH2CH2NHBoc), 3.35 (2H, br, m, ArCH2CH2NHBoc), 3.61 (2H, s, ArCH2CO2H), 4.57 (1H, br, s, ArCH2CH 2 NHBoc), 7.14 (2H, d, J=7.7 Hz, ArH), 7.21 (2H, d, J=7.7 Hz, ArH); m/e (CI-) 278 (100%, m-H).

후처리

  1. customThe organic solvent was removed under vacuum
  2. additionthe residue was diluted with water (40 ml)
  3. extractionextracted with ethyl acetate (2×30 ml)
  4. washThe combined extracts were washed with brine (1×30 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

출처 및 근거

ORD 기록
ord-e232ebfd089d43378c8fc9c3425059b9
출처 데이터셋
uspto-grants-1993_07
특허 번호
US05231102

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