Acetic Acid → HCID 86589978, compound

HRID 1793257Notes

Reaction equation

HRID 1793257 reaction equation
C(N)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C.[BH3-]C#N.[Na+].[C:23]([Si:27]([CH3:80])([CH3:79])[O:28][C@@H:29]1[C@@:33]([CH:53]([NH:62][CH2:63][C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[NH:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)([CH2:34][O:35][Si:36]([C:49]([CH3:52])([CH3:51])[CH3:50])([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:32][C@@H:31]([N:70]2[CH:78]=[C:76](C)[C:74](=[O:75])[NH:73][C:71]2=[O:72])[CH2:30]1)([CH3:26])([CH3:25])[CH3:24]>C(#N)C>[C:23]([Si:27]([CH3:80])([CH3:79])[O:28][C@@H:29]1[C@@:33]([CH:53]([NH:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[NH:62][CH2:63][C:64]2[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=2)([CH2:34][O:35][Si:36]([C:49]([CH3:52])([CH3:51])[CH3:50])([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[O:32][C@@H:31]([N:70]2[CH:78]=[CH:76][C:74](=[O:75])[NH:73][C:71]2=[O:72])[CH2:30]1)([CH3:24])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7036BenzhydrylamineHCID 5003444Sodium cyanoborohydrideHCID 86589977HCID 86589977, compound

Product 1

HCID 86589978HCID 86589978, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3′-O-[(tertbutyl)dimethylsilyl]-5′-O-[(tertbutyl)diphenylsilyl]-4′-C-formyl-2-deoxyuridine (10) (Yang et al; Tetrahedron Letters 1992, 33, 37–40.) (0.15 g, 0.25 mmol) was treated with Ph2CHNH2 (0.07 g, 0.37 mmol, 0.064 mL), glacial acetic acid (0.015 g, 0.26 mmol, 0.015 mL) and NaBH3CN (0.023 g, 0.37 mmol) in acetonitrile (1 mL) according to the procedure used for the preparation of compound (2). The title compound (11) was obtained as clear, viscous oil (0.13 g, 69%). δH(300 MHz, CDCl3) 8.02(1H, s, br, N3—H), 7.81(1H, d, H-6), 7.69–7.18(20H, m, Ph2CHNH, tBuSiPh2), 6.32(1H, dd, H-1′), 5.30(1H, d, H-5), 4.67(1H, s, Ph2CHNH), 4.61(1H, dd, H-3′), 4.02(1H, d, H-5′), 3.87(1H, d, H-5′), 2.69(1H, d, 4′-C—CH2), 2.53(1H, d, 4′-C—CH2), 2.37(1H, m, H-2′), 2.17(1H, m, H-2′), 1.10(9H, s, tBuSiPh2), 0.75(9H, s, tBuSiMe2), 0.01(6H, s, tBuSiMe2); ES +ve m/z 776(M+H)+.

Sources & evidence

ORD record
ord-8d5e97497e1d41aab531e4ebb94a2526
Source dataset
uspto-grants-2006_07
Patent number
US07078499B2

Reaction notes

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