Lanthanum tris(trifluoromethanesulfonate) → HCID 89852314, compound

HRID 627189Notes

Reaction equation

HRID 627189 reaction equation
N1(C([O-])=O)CCC=CC1.[Si:10]([O:17][CH2:18][C@@H:19]1[CH:24]=[C:23]([CH2:25][OH:26])[C:22](=[O:27])[CH2:21][N:20]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].ClC(Cl)(Cl)C(=N)O[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[La+3]>C1(C)C=CC=CC=1>[Si:10]([O:17][CH2:18][C@@H:19]1[CH:24]=[C:23]([CH2:25][O:26][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[C:22](=[O:27])[CH2:21][N:20]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 2733938Lanthanum tris(trifluoromethanesulfonate)HCID 110872634-Methoxybenzyl 2,2,2-TrichloroacetimidateHCID 21691317HCID 21691317, compoundHCID 89852514HCID 89852514, compound

Product 1

HCID 89852314HCID 89852314, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (2S)-tert-butyl 5-hydroxy-4-(hydroxymethyl)-2-(isopropyldimethylsilyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 117, 13.0 g, 34.99 mmol) in toluene (150 mL) was added 4-methoxybenzyl 2,2,2-trichloroacetimidate (7.65 mL, 10.42 g, 36.74 mmol) and La(OTf)3 (205 mg, 0.35 mmol). The mixture was stirred at 50° C. for 4 h. Aqueous work-up with ethyl acetate and the organic layer was dried over MgSO4 to afford the crude product.

Workup

  1. dry with materialAqueous work-up with ethyl acetate and the organic layer was dried over MgSO4

Sources & evidence

ORD record
ord-2ae5512d9f3045a6829cdd18e4830b2c
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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