Sulfuric Acid → HCID 67462821, 화합물

HRID 2207141노트

반응식

HRID 2207141 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([C:29]([OH:31])=[O:30])[CH2:20][O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(O[C:36]([CH3:39])([CH3:38])[CH3:37])(=O)C.S(=O)(=O)(O)O>ClCCl>[C:36]([O:30][C:29](=[O:31])[C@@H:19]([CH2:20][O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[NH:18][C:16]([O:15][CH2:14][CH:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:17])([CH3:39])([CH3:38])[CH3:37]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 10908tert-Butyl acetateHCID 7019719Fmoc-D-Ser(Bzl)-OH

생성물 1

HCID 67462821HCID 67462821, 화합물수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N-[(9H-Fluoren-9-yl)methoxycarbonyl]-O-(benzyl)-D-serine (0.710 g, 1.70 mmole) in dichloromethane (8 mL) was treated with t-butyl acetate (3 mL) and concentrated sulfuric acid (40 μL) in a sealed flask at 0° C. Upon completion (TLC), the reaction was quenched with of dichloromethane (10 mL) and saturated aqueous potassium bicarbonate (15 mL). The organic layer was washed with distilled water, and evaporated. The resulting residue was purified by flash column chromatography (98:2 dichloromethane/methanol) to yield the title compound as a colorless oil (0.292 g, 77%); 1H NMR (CDCl3) δ 1.44 (s, 9H); 3.68 (dd, J=2.9 Hz, J=9.3 Hz, 1H); 3.87 (dd, J=2.9 Hz, J=9.3 Hz, 1H); 4.22 (t, J=7.1 Hz, 1H); 4.30-4.60 (m, 5H); 5.64-5.67 (m, 1H); 7.25-7.39 (m, 9H); 7.58-7.61 (m, 2H); 7.73-7.76 (m, 2H).

후처리

  1. customUpon completion (TLC), the reaction was quenched with of dichloromethane (10 mL) and saturated aqueous potassium bicarbonate (15 mL)
  2. washThe organic layer was washed with distilled water
  3. customevaporated
  4. customThe resulting residue was purified by flash column chromatography (98:2 dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-0fd8ccaf45c04a32ab4bb4e6e258e7a4
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376424B2

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