Methanol → 2'-Deoxy-2'-(N-Fmoc-beta-alanineamido)uridine

HRID 1987788Notes

Reaction equation

HRID 1987788 reaction equation
CCO[CH:4]1[N:13](C(OCC)=O)C2C(=CC=CC=2)[CH:6]=[CH:5]1.[NH2:19][C@@H:20]1[C@H:24]([OH:25])[C@@H:23]([CH2:26][OH:27])[O:22][C@H:21]1[N:28]1[CH:35]=[CH:34][C:32](=[O:33])[NH:31][C:29]1=[O:30].[C:36](NCCC(O)=O)([O:38][CH2:39][CH:40]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]2[C:41]1=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:37].C[OH:60]>ClCCl>[C:36]([N:19]([C@@H:20]1[C@H:24]([OH:25])[C@@H:23]([CH2:26][OH:27])[O:22][C@H:21]1[N:28]1[CH:35]=[CH:34][C:32](=[O:33])[NH:31][C:29]1=[O:30])[C:6](=[O:60])[CH2:5][CH2:4][NH2:13])([O:38][CH2:39][CH:40]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]2[C:41]1=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:37]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 2724630N-Fluorenylmethoxycarbonyl-I2-alanineHCID 64824792'-Amino-2'-deoxyuridine

Product 1

HCID 686614692'-Deoxy-2'-(N-Fmoc-beta-alanineamido)uridineYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Referring to FIG. 10, EEDQ (4.2 g, 17 mmol) was added to the solution of 2′-amino-2′-deoxy uridine (4 g, 16.45 mmol) and N-FMOC-beta-alanine (5.1 g, 16.45 mmol) in methanol and the reaction mixture was boiled for two hours. Subsequent flash chromatography on silica using a linear gradient of methanol (5% to 10%) in dichloromethane afforded 6 g of 2′-Deoxy-2′-(N-Fmoc-beta-alanineamido)uridine (77%). 1H NMR (CDCl3-DMSO-d6) d 10.398 (s, 1H, N3-H), 6.98-7.63 (m, H6, Fmoc), 6.16 (t, 1H, NHFmoc), 5.73 (d, 1H, H1′, J1′,2′ 8.4), 5.34 (d, 1H, H5), 4.22 (m, 1H, 2′-H) 3.98 (dd 2H, CH2), 3.88 (m, 1H, 3′-H), 3.77 (br s, 1H, 4′-H), 3.43 (m, 2H, 5′-CH2), 3.1 (m, 2H, CH2NHFmoc), 2.07 (t, 2H, CH2CO).

Sources & evidence

ORD record
ord-016a2068bf6e444d80ccf70bea14caaf
Source dataset
uspto-grants-2009_06
Patent number
US07553830B2

Reaction notes

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