Sodium Cyanide → (4R ,5R)-5-(4-chloro-3-trifluoromethyl-phenyl)-4-(toluene-4-sulfonyl)-4,5-dihydro-oxazole

HRID 411640

Reaction equation

[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[S:14]([CH2:24][N+:25]#[C-:26])([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15].[C-]#N.[Na+]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C@H:6]2[O:7][CH:26]=[N:25][C@@H:24]2[S:14]([C:17]2[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:4][C:3]=1[C:10]([F:11])([F:12])[F:13]

Participants

Reactant 3

HCID 8929Sodium Cyanide

HCID 1186424-Chloro-3-(trifluoromethyl)benzaldehyde

HCID 161915Tosylmethyl isocyanide

Product 1

HCID 69556945(4R *,5R*)-5-(4-chloro-3-trifluoromethyl-phenyl)-4-(toluene-4-sulfonyl)-4,5-dihydro-oxazole

Procedure

In a manner analogous to Preparation 1, 4-chloro-3-(trifluoromethyl)benzaldehyde (0.31 g, 1.47 mmol), tosylmethylisocyanide (0.27 g, 1.40 mmol) and NaCN (6.9 mg, 0.14 mmol) gave the desired compound as a tan solid. MS(ES+) m/z 404.5 (M+H+).

Sources & evidence

ORD record: ord-2062fb24d3e14162a441c15b1be6598e
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559172B1

Linked notes

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