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

HRID 473586

반응식

HRID 473586 반응식
[CH2:1](OC(=NOCCN(C)C[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2C)[C@H](O)[C@@H]1O)C)C.[C:31]([CH2:36][CH2:37][N:38]([CH3:58])[CH2:39][C@H:40]1[O:44][C@@H:43]([N:45]2[C:54]3[N:53]=[CH:52][N:51]=[C:49]([NH2:50])[C:48]=3[N:47]=[C:46]2[CH3:55])[C@H:42]([OH:56])[C@@H:41]1[OH:57])([O:33][CH2:34][CH3:35])=[O:32].CNC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2CC)[C@H](O)[C@@H]1O.ClCCC(OCC)=O.CCN(C(C)C)C(C)C>CN(C=O)C>[C:31]([CH2:36][CH2:37][N:38]([CH3:58])[CH2:39][C@H:40]1[O:44][C@@H:43]([N:45]2[C:54]3[N:53]=[CH:52][N:51]=[C:49]([NH2:50])[C:48]=3[N:47]=[C:46]2[CH2:55][CH3:1])[C@H:42]([OH:56])[C@@H:41]1[OH:57])([O:33][CH2:34][CH3:35])=[O:32]

참가 물질

7

반응물 5

HCID 69341Ethyl 3-chloropropionateHCID 81531DiisopropylethylamineHCID 252320015'-Deoxy-5'-methylamino-8-ethyladenosineHCID 252332505'-[(carboethoxyethyl)methyamino]-5'-Deoxy-8-methyladenosineHCID 866496695'-Deoxy-5'-[[2-[[(1-ethoxyethylidene)amino]oxy]ethyl]methylamino]-8-methyladenosine

생성물 1

HCID 252323655'-[(carboethoxyethyl)methyamino]-5'-Deoxy-8-ethyladenosine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Compound 33b was prepared by the same procedure as described for the preparation of 6a and 33a using 4b (260 mg, 0.84 mm), ethyl 3-chloropropionate (138 mg, 1.0 mm), DIEA (53 mg, 0.07 ml, 0.41 mm), and DMF (4 ml). After column chromatography (elution with 7:1:0.1 chloroform:methanol:NH4OH), a glassy sticky solid was obtained: yield 153 mg (44%), MS: m/z 409 (M+H)+; 1HNMR (DMSO-d6) δ 8.08 (s, 1H, H-2), 7.10 (bs, 2H, 6-NH2), 5.71 (d, 1H, H-1′, J1′,2′=5.5 Hz), 5.32 (bd, 1H, OH-2′, J2′-2′OH=5.0 Hz), 5.16 (bd, 1H, OH-3′, J3′-3′OH=5.1 Hz), 5.12 (ddd, 1H, H-2′, J1′,2′=5.5 Hz, J2′,3′=5.7 Hz, J2′-2′OH=5.0 Hz), 4.14 (ddd, 1H, H-3′, J2′,3′=5.7 Hz, J3′,4′=4.1 Hz, J3′-3′OH=5.1 Hz), 4.01 (q, 2H, CH3—CH2), 3.91-3.98 (m, 1H, H-4′), 2.87 (q, 2H, CH2 of 8-Et), 2.71-2.79 (m, 1H, 5′-CH2), 2.51-2.65 (m, 3H, 5′-CH2, CO—CH2), 2.38 (t, 2H, NCH3—CH2), 2.16 (bs, 3H, N—CH3), 1.30 (t, 31-1, CH3 of 8-Et), 1.15 (t, 3H, OCH2—CH3).

후처리

  1. washAfter column chromatography (elution with 7:1:0.1 chloroform:methanol:NH4OH)
  2. customa glassy sticky solid was obtained

출처 및 근거

ORD 기록
ord-795ad05088c846f3abd6d0c9b917b4fc
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637485B2

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