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

HRID 484450ノート

反応式

HRID 484450 の反応式
[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]

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 19747487HCID 19747487、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e232ebfd089d43378c8fc9c3425059b9
出典データセット
uspto-grants-1993_07
特許番号
US05231102

反応ノート

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