Trimethylsilyldiazomethane → methyl N-[(5-chlorothien-2-yl)sulfonyl]-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-dl-norvalinate

HRID 1985970Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][CH:11]([C:23]([OH:25])=[O:24])[CH:12]([CH2:18][C:19]([F:22])([F:21])[F:20])[CH2:13][C:14]([F:17])([F:16])[F:15])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:27]>C(Cl)Cl.CO>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][CH:11]([C:23]([O:25][CH3:27])=[O:24])[CH:12]([CH2:13][C:14]([F:16])([F:17])[F:15])[CH2:18][C:19]([F:22])([F:21])[F:20])(=[O:8])=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of N-[(5-chlorothien-2-yl)sulfonyl]-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-dl-norvaline (1.3 g, 5.23 mmol) in CH2Cl2:MeOH (4:1) TMSCHN2 (6 mL, 12 mmol) was added dropwise over 10 min at 0° C. until a neon yellow color persisted. When the dropwise addition was completed, the reaction mixture was allowed to warm to 25° C. over 19 h. The solvent was removed in vacuo to obtain methyl N-[(5-chlorothien-2-yl)sulfonyl]-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-dl-norvalinate (0.5 g, 37.31%). Mass Spectrum (−ESI): 445 (M−H)−.

Workup

additionWhen the dropwise addition
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-7eae855ac7774659bed3aafd913c2af2
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547725B2

Reaction notes

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