Water → [2-(2,6-Dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-carbamic acid tert-butyl ester

HRID 2103456

반응식

HRID 2103456 반응식
C(N(C(C)C)CC)(C)C.CO[C:12](=[O:32])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:14]=1[C:28]([O:30]C)=O.Cl.[NH2:34][CH:35]1[CH2:41][CH2:40][C:39](=[O:42])[NH:38][C:36]1=[O:37].O>CN(C=O)C>[C:24]([O:23][C:21](=[O:22])[NH:20][CH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]2[C:14]=1[C:28](=[O:30])[N:34]([CH:35]1[CH2:41][CH2:40][C:39](=[O:42])[NH:38][C:36]1=[O:37])[C:12]2=[O:32])([CH3:25])([CH3:26])[CH3:27]

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 21988573Methyl-3-[(t-butoxycarbonylamino)methyl]-2-(methoxycarbonyl)benzoate

생성물 1

HCID 9908253[2-(2,6-Dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

Diisopropylethylamine (3.20 g, 25 mmol) was added to a stirred suspension of methyl-3-[(t-butoxycarbonylamino)methyl]-2-(methoxycarbonyl)benzoate (8.00 g, 25 mmol) and aminoglutarimide hydrochloride (4.07 g, 25 mmol) in DMF (60 ml). The mixture was heated to 120° C. for 24 hours and then cooled to room temperature. The mixture was poured into cold water (300 ml) and extracted with ethyl acetate (4×100 ml each). The combined ethyl acetate extracts were washed with water (2×50 ml), brine (50 ml) and dried. Solvent was removed in vacuo and the product purified by flash chromatography (dichloromethane/ethyl acetate 8 to 2) to yield 4.66 g of recovered starting material and 3.31 g (82%) of the product as a white solid: mp 180-182° C.; 1H NMR (CDCl3) δ 8.51 (s, 1H), 7.81-7.67 (m, 3H), 5.54 (b, 1H), 5.03-4.96 (dd, J=5.2 and 11.2 Hz, 1H), 4.66 (d, J=6.3 Hz, 2H), 2.95-2.74 (m, 3H), 2.18-2.14 (m, 1H), 1.43 (s, 9H); 13C NMR (CDCl3) δ 170.99, 168.08, 167.95, 167.07, 155.86, 139.17, 135.00, 134.61, 132.15, 128.22, 122.82, 79.81, 49.21, 40.53, 31.33, 28.32, 22.58; Anal. Calcd for C19H21N3O6: C, 58.91; H, 5.46; N, 10.85. Found: C, 59.08; H, 5.51; N, 10.69.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (4×100 ml each)
  3. washThe combined ethyl acetate extracts were washed with water (2×50 ml), brine (50 ml)
  4. customdried
  5. customSolvent was removed in vacuo
  6. customthe product purified by flash chromatography (dichloromethane/ethyl acetate 8 to 2)
  7. customto yield 4.66 g
  8. customof recovered

출처 및 근거

ORD 기록
ord-d1192d635ce444668929ae5b0327cf9f
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576104B2

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