Ethyl chloroacetate → 5'-[(Carboethoxymethyl)methyamino]-5'-deoxy-8-methyladenosine

HRID 473587

반응식

HRID 473587 반응식
C(OC(=N[O:7][CH2:8][CH2:9][N:10]([CH3:30])[CH2:11][C@H:12]1[O:16][C@@H:15]([N:17]2[C:26]3[N:25]=[CH:24][N:23]=[C:21]([NH2:22])[C:20]=3[N:19]=[C:18]2[CH3:27])[C@H:14]([OH:28])[C@@H:13]1[OH:29])C)C.CNC[C@H]1[O:38][C@@H:37](N2C3N=CN=C(N)C=3N=C2C)[C@H:36](O)[C@@H]1O.ClCC(OCC)=O.CCN(C(C)C)C(C)C>CN(C=O)C>[C:8]([CH2:9][N:10]([CH3:30])[CH2:11][C@H:12]1[O:16][C@@H:15]([N:17]2[C:26]3[N:25]=[CH:24][N:23]=[C:21]([NH2:22])[C:20]=3[N:19]=[C:18]2[CH3:27])[C@H:14]([OH:28])[C@@H:13]1[OH:29])([O:38][CH2:37][CH3:36])=[O:7]

참가 물질

6

반응물 4

HCID 7751Ethyl chloroacetateHCID 81531DiisopropylethylamineHCID 252327175'-Deoxy-5'-methylamino-8-methyladenosineHCID 866496695'-Deoxy-5'-[[2-[[(1-ethoxyethylidene)amino]oxy]ethyl]methylamino]-8-methyladenosine

생성물 1

HCID 252332515'-[(Carboethoxymethyl)methyamino]-5'-deoxy-8-methyladenosine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Compound 35 was prepared by the same procedure as described for the preparation of 6a using 4a (415 mg, 1.41 mm), ethyl chloroacetate (207 mg, 0.18 ml, 1.68 mm), DIEA (91 mg, 0.12 ml, 0.70 mm), and DMF (5 ml): yield 204 mg (38%), MS: m/z 381 (M+H)+; 1HNMR (DMSO-d6) δ 8.06 (s, 1H, H-2), 7.11 (bs, 2H, 6-NH2), 5.73 (d, 1H, H-1′, J1′,2′=5.4 Hz), 5.33 (bd, 1H, OH-2′, J2′-2′OH=4.7 Hz), 5.19 (bd, 1H, OH-3′, J3′-3′OH=4.9 Hz), 5.03 (ddd, 1H, H-2′, J1′,2′=5.4 Hz, J2′,3′=5.7 Hz, J2′-2′OH=4.7 Hz), 4.17 (ddd, 1H, H-3′, J2′,3′=5.7 Hz, J3′,4′=4.4 Hz, J3′-3′OH=4.9 Hz), 4.02 (q, 2H, CH3—CH2), 3.92-3.99 (m, 1H, H-4′), 3.27 (bs, 2H, NCH3—CH2), 2.83-2.90 (m, 1H, 5′-CH2), 2.70-2.79 (m, 1H, 5′-CH2), 2.53 (s, 3H, 8-CH3), 2.31 (s, 3H, N—CH3), 1.13 (t, 3H, OCH2—CH3); UV λmax, nm, pH 1, 258.9 (∈ 16,100), pH 7, 260 (∈ 15,900), pH 13, 260.1 (∈ 16,200).

출처 및 근거

ORD 기록
ord-7119ee6e7c414467b7f98673e5d0d5ff
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637485B2

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