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Methanol → Triethylammonium 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxyethyl)-5-methyluridine-3'-O-succinate

HRID 891222
Notes
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Reaction equation

HRID 891222 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C@@H:6]1[C@H:10]([OH:11])[C@@H:9]([CH2:12][OH:13])[O:8][C@H:7]1[N:14]1[CH:21]=[C:20]([CH3:22])[C:18](=[O:19])[NH:17][C:15]1=[O:16].[CH3:23][O:24][C:25]1[CH:46]=[CH:45][C:28]([C:29](Cl)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[CH:27][CH:26]=1.C[OH:48].[C:49]1(=[O:55])[O:54][C:52](=[O:53])[CH2:51][CH2:50]1>N1C(C)=CC=CC=1C.C(#N)C.C(N(CC)CC)C>[CH3:23][O:24][C:25]1[CH:46]=[CH:45][C:28]([C:29]([O:13][CH2:12][C@H:9]2[O:8][C@@H:7]([N:14]3[CH:21]=[C:20]([CH3:22])[C:18](=[O:19])[NH:17][C:15]3=[O:16])[C@H:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[C@@H:10]2[O:11][CH:51]([C:52]([O-:48])=[O:53])[CH2:50][C:49]([O-:54])=[O:55])([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[CH:27][CH:26]=1.[CH2:21]([NH+:14]([CH2:7][CH3:6])[CH2:15][CH3:23])[CH3:20].[CH2:21]([NH+:14]([CH2:7][CH3:6])[CH2:15][CH3:23])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 887MethanolHCID 7922Succinic anhydrideHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 112439882'-O-(2-Methoxyethyl)-5-methyl-uridine

Product 1

HCID 86593945Triethylammonium 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-methoxyethyl)-5-methyluridine-3'-O-succinateYield 90%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 79372,6-LutidineSolventHCID 8471TriethylamineSolvent

Procedure

2′-O-(2-methoxyethyl)-5-methyluridine (MOE T, 15.8 g, 50 mmol) was dissolved in 2,6-lutidine (23.3 ml) and acetonitrile (150 ml). 4,4′-Dimethoxytrityl chloride (DMTCl, 18.6 g, 55 mmol) was added. The mixture was stirred at room temperature for 30 min. and methanol (MeOH, 0.2 ml) was added. After 10 min., triethylamine (20 ml) and succinic anhydride (15 g) were added and the mixture was stirred overnight. The mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane (200 ml) and washed with triethylammonium phosphate (0.5 M, pH 7, 3×100 ml). The organic layer was dried (Na2SO4) and evaporated to approximately 100 ml. Hexane (150 ml) was added. The mixture was shaken for 5 min. and the supernatant was decanted. The residue was dried to give a yellow solid (36.8 g, 90%).

Workup

  1. waitAfter 10 min.
  2. stirringthe mixture was stirred overnight
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (200 ml)
  5. washwashed with triethylammonium phosphate (0.5 M, pH 7, 3×100 ml)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customevaporated to approximately 100 ml
  8. additionHexane (150 ml) was added
  9. stirringThe mixture was shaken for 5 min.
  10. customthe supernatant was decanted
  11. customThe residue was dried

Sources & evidence

ORD record
ord-31150971ef5548aca6bcf0ff9556428b
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07002006B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes