HCID 54695617, compound → HCID 68569908, compound

HRID 1435107Notes

Reaction equation

HRID 1435107 reaction equation
[N:1]1([C:10]2[S:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[C:12]([OH:19])[CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Cl:20][C:21]1[C:26]([O:27][Si](C(C)(C)C)(C)C)=[CH:25][CH:24]=[CH:23][C:22]=1[C@@H:35](O)[CH3:36]>>[N:1]1([C:10]2[S:14][C:13]([C:15]([O:17][CH3:18])=[O:16])=[C:12]([O:19][C@@H:35]([C:22]3[CH:23]=[CH:24][CH:25]=[C:26]([OH:27])[C:21]=3[Cl:20])[CH3:36])[CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

3

Reactant 2

HCID 54695617HCID 54695617, compoundHCID 57937626HCID 57937626, compound2×

Product 1

HCID 68569908HCID 68569908, compoundYield 73.3%

Procedure

Title compound (2.2 g) was prepared from methyl 5-(1H-benzimidazol-1-yl)-3-hydroxy-2-thiophenecarboxylate (J. Heterocyclic Chem., 1987, 24, 1301-1303) (1.9 g, 7.0 mmol) and (1S)-1-(2-chloro-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}phenyl)ethanol (Intermediate 17, 2.0 g, 7.0 mmol) using a procedure analogous to Intermediate 2, Step C.

Sources & evidence

ORD record
ord-9633f67c773848d3a7a89182699fd28b
Source dataset
uspto-grants-2009_11
Patent number
US07615643B2

Reaction notes

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