Hydrochloric Acid → (5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-ethanoic acid

HRID 1755817ノート

反応式

HRID 1755817 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]([O:24]C)=[O:23])[C:17](=[O:26])[CH:16]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:15]=1)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]([OH:24])=[O:23])[C:17](=[O:26])[CH:16]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:15]=1)[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86748875methyl (5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-ethanoate

生成物 1

HCID 54027587(5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-ethanoic acid

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of the above ester (35) (1.2 g) in dioxane (12 mL) was added a solution of NaOH (5.3 mL, 1N in H2O). After stirring for 4 h at room temperature 1N HCl (5.3 mL) was added and the reaction extracted with ethyl acetate, washed with saturated NaCl, dried over MgSO4 and evaporated. The product (37) was obtained by flash chromatography (silica gel, 98:2:0.1 CHCl3 :MeOH:HOAc) (1.0 g, 86%). TLC Rf 0.53 (95:4:1 CHCl3 :MeOH:HOAc); MS DC I/NH3 (M+H)+ =436.3; 1H NMR (CDCl3) δ1.13(3H, d, J=7 Hz ), 1.6-3.3 (9H, m), 3.65 (1H, m), 4.1 (1H, br m), 5.1 (2H, s), 5.45(1H, d), 7.2(5H, s), 7.35(5H, s), 10.65 (1H, br s).

後処理

  1. additionwas added
  2. extractionthe reaction extracted with ethyl acetate
  3. washwashed with saturated NaCl
  4. dry with materialdried over MgSO4
  5. customevaporated

出典と根拠

ORDレコード
ord-a1a359c522584514871aa836d8ce3a96
出典データセット
uspto-grants-1995_08
特許番号
US05438118

反応ノート

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