Ethanol → 3'-O-Methanesulfonyl-5'-O-trityl-2'-deoxyuridine

HRID 2372519Notes

Reaction equation

[C:1]([O:20][CH2:21][C@H:22]1[O:26][C@@H:25]([N:27]2[CH:34]=[CH:33][C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24][C@@H:23]1[OH:35])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38].C(Cl)(Cl)Cl.CCO>N1C=CC=CC=1>[CH3:36][S:37]([O:35][C@@H:23]1[C@@H:22]([CH2:21][O:20][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:26][C@@H:25]([N:27]2[CH:34]=[CH:33][C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:24]1)(=[O:39])=[O:38]

Participants

Conditions

Temperature: 4 °C

Procedure

The product of Example 1 (59 g, 0.13 mol) was dissolved at room temperature in 120 mL of pyridine. The solution was put into an ice bath and 29 mL of methanesulfonyl chloride (0.34 mol) was added dropwise. The resulting solution was allowed to stir at 4° C. for 24 hours. The reaction mixture was added in three portions at a slow flow rate into a blender as described previously. The pea-green solid was collected by filtration, washed twice with 2 L of water, and dried to yield 58 g (93%). The compound started to soften at 85° C. and melted at 106-108° C. Rf =0.62 (CHCl3 --EtOH, 10:1). Anal. (C29H28N2O7S).

Workup

customThe solution was put into an ice bath
additionThe reaction mixture was added in three portions at a slow flow rate into a blender
filtrationThe pea-green solid was collected by filtration
washwashed twice with 2 L of water
customdried
customto yield 58 g (93%)
customto soften at 85° C.

Sources & evidence

ORD record: ord-3ebd16bc27884e7cb445390ed9808b90
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05099010

Reaction notes

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