Ethyl 3-chloropropionate → 5'-[(carboethoxyethyl)methyamino]-5'-Deoxy-8-methyladenosine

HRID 473575

반응식

HRID 473575 반응식
[CH3:1][NH:2][CH2:3][C@H:4]1[O:8][C@@H:7]([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13]([NH2:14])[C:12]=3[N:11]=[C:10]2[CH3:19])[C@H:6]([OH:20])[C@@H:5]1[OH:21].Cl[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].CCN(C(C)C)C(C)C>CN(C=O)C>[C:25]([CH2:24][CH2:23][N:2]([CH3:1])[CH2:3][C@H:4]1[O:8][C@@H:7]([N:9]2[C:18]3[N:17]=[CH:16][N:15]=[C:13]([NH2:14])[C:12]=3[N:11]=[C:10]2[CH3:19])[C@H:6]([OH:20])[C@@H:5]1[OH:21])([O:27][CH2:28][CH3:29])=[O:26]

참가 물질

5

반응물 3

HCID 69341Ethyl 3-chloropropionateHCID 81531DiisopropylethylamineHCID 252327175'-Deoxy-5'-methylamino-8-methyladenosine

생성물 1

HCID 252332505'-[(carboethoxyethyl)methyamino]-5'-Deoxy-8-methyladenosine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A mixture of 4a (500 mg, 1.69 mmol), ethyl 3-chloropropionate (270 mg, 1.97 mmol), DIEA (109 mg, 0.14 mL, 0.84 mmol), and DMF (5 mL) was heated at 60° C. for 2 days. Starting material remained but since the solution was getting darker, heating was stopped. The reaction mixture was concentrated to dryness. The product was purified by column chromatography (7:1:0.1 chloroform:methanol:NH4OH) to give a sticky solid: yield 210 mg (31%); MS m/z 395 (M+H)+; 1HNMR (DMSO-d6) δ 8.08 (s, 1H, H-2), 7.11 (bs, 2H, 6-NH2), 5.74 (d, 1H, H-1′, J1′,2′=5.6 Hz), 5.33 (bd, 1H, OH-2′), 5.16 (bd, 111, OH-3′), 5.12 (bdd, 1H, H-2′, J1′,2′=5.6 Hz, J2′,3′=5.5 Hz), 4.21 (bdd, 1H, H-3′, J2′,3′=5.5 Hz, J3′,4′=4.3 Hz), 4.01 (q, 2H, OCH2CH3), 3.91-4.00 (m, 1H, H-4′), 2.70-2.77 (m, 1H, 5′-CH2), 2.54-2.66 (m, 3H, 5′-CH2, CO—CH2), 2.53 (s, 3H, 8-CH3), 2.38 (t, 2H, N(CH3)—CH2), 2.16 (bs, 3H, N—CH3), 1.15 (t, 3H, OCH2CH3).

후처리

  1. temperatureheating
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customThe product was purified by column chromatography (7:1:0.1 chloroform:methanol:NH4OH)
  4. customto give a sticky solid

출처 및 근거

ORD 기록
ord-5e323b7547ab4f3eba2f376f6295eac2
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637485B2

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