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

HRID 473587

反応式

HRID 473587 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

出典と根拠

ORDレコード
ord-7119ee6e7c414467b7f98673e5d0d5ff
出典データセット
uspto-grants-2014_01
特許番号
US08637485B2

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