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

HRID 473577Notes

Reaction equation

HRID 473577 reaction equation
C(C[CH2:7][N:8]([CH3:28])[CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[C:24]3[N:23]=[CH:22][N:21]=[C:19]([NH2:20])[C:18]=3[N:17]=[C:16]2[CH3:25])[C@H:12]([OH:26])[C@@H:11]1[OH:27])(OCC)=O.CNC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2C)[C@H](O)[C@@H]1O.ClC[C:52]([O:54][CH2:55][CH3:56])=[O:53].CCN(C(C)C)C(C)C>CN(C=O)C>[C:52]([CH2:7][N:8]([CH3:28])[CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[C:24]3[N:23]=[CH:22][N:21]=[C:19]([NH2:20])[C:18]=3[N:17]=[C:16]2[CH3:25])[C@H:12]([OH:26])[C@@H:11]1[OH:27])([O:54][CH2:55][CH3:56])=[O:53]

Participants

6

Reactant 4

HCID 7751Ethyl chloroacetateHCID 81531DiisopropylethylamineHCID 252327175'-Deoxy-5'-methylamino-8-methyladenosineHCID 252332505'-[(carboethoxyethyl)methyamino]-5'-Deoxy-8-methyladenosine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 13c was prepared by the same procedure as described for the preparation of 13a using 4a (415 mg, 1.41 mmol), ethyl chloroacetate (207 mg, 0.18 mL, 1.68 mmol), DIEA (91 mg, 0.12 mL, 0.70 mmol), 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, OCH2CH3), 3.92-3.99 (m, 1H, H-4′), 3.27 (bs, 2H, N(CH3)—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, OCH2CH3); UV λmax, nm, pH 1, 258.9 (∈ 16,100), pH 7, 260 (∈ 15,900), pH 13, 260.1 (∈ 16,200). Anal. (C16H24N6O5.0.5CHCl3.0.3CH3OH) C, H, N.

Sources & evidence

ORD record
ord-0d4a718422f447bd86d1e5639be2755b
Source dataset
uspto-grants-2014_01
Patent number
US08637485B2

Reaction notes

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