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

HRID 473587

Reaction equation

HRID 473587 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Sources & evidence

ORD record
ord-7119ee6e7c414467b7f98673e5d0d5ff
Source dataset
uspto-grants-2014_01
Patent number
US08637485B2

Linked notes

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