Sodium hydride → HCID 69414220, compound

HRID 853045Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=2)=[O:7])[CH3:4].[C:21]([O:25][C:26]([N:28]1[CH2:32][C@H:31]([CH3:33])OS1(=O)=O)=[O:27])([CH3:24])([CH3:23])[CH3:22]>CN(C)C=O>[CH2:3]([O:5][C:6]([C:8]1[N:9]([C@H:31]([CH3:33])[CH2:32][NH:28][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([C:17]([F:20])([F:18])[F:19])[CH:11]=2)=[O:7])[CH3:4]

Participants

Conditions

Temperature: 5 °C

Procedure

Sodium hydride (0.75 g, 17 mmol) was suspended in N,N-dimethylformamide (15 mL) and a solution of 6-trifluoromethyl-1H-indole-2-carboxylic acid ethyl ester (3.6 g, 14 mmol) in N,N-dimethylformamide (15 mL) was added with cooling at 5° C. After 1 h (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (4.0 g, 17 mmol) was added and the solution was allowed to reach room temperature over the weekend. The solution was partitioned between ice water (600 mL) and diethylether (2-×250 mL). The organic layer was washed with ice water and brine, dried (MgSO4), and evaporated. Chromatography on silica gel with n-hexane/diethylether (4:1) yielded the title product as yellow oil (5.1 g, 88%). ISP-MS: m/e=415.3 (M+H+), αD20=−29.6

Workup

customto reach room temperature over the weekend
customThe solution was partitioned between ice water (600 mL) and diethylether (2-×250 mL)
washThe organic layer was washed with ice water and brine
dry with materialdried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-8ec37c4ca20e4a04ba5696ac3869d3b3
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253281B2

Reaction notes

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