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

HRID 473576

Reaction equation

HRID 473576 reaction equation
[C:1]([CH2:6][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:3][CH2:4][CH3:5])=[O:2].[CH3:29]NC[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:1]([CH2:6][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[CH2:25][CH3:29])[C@H:12]([OH:26])[C@@H:11]1[OH:27])([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 69341Ethyl 3-chloropropionateHCID 81531DiisopropylethylamineHCID 252320015'-Deoxy-5'-methylamino-8-ethyladenosineHCID 252332505'-[(carboethoxyethyl)methyamino]-5'-Deoxy-8-methyladenosine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 13b was prepared by the same procedure as described for the preparation of 13a using 4b (260 mg, 0.84 mmol), ethyl 3-chloropropionate (138 mg, 1.0 mmol), DIEA (53 mg, 0.07 mL, 0.41 mmol), 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, OCH2CH3), 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, N(CH3)—CH2), 2.16 (bs, 3H, N—CH3), 1.30 (t, 3H, CH3 of 8-Et), 1.15 (t, 3H, OCH2CH3).

Workup

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

Sources & evidence

ORD record
ord-ba6e387aa38e462799e8e9e94b2550cc
Source dataset
uspto-grants-2014_01
Patent number
US08637485B2

Linked notes

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