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

HRID 1755817노트

반응식

HRID 1755817 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-a1a359c522584514871aa836d8ce3a96
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05438118

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