5-Chlorothiophene-2-sulfonyl chloride → GSI-136

HRID 2092959Notes

Reaction equation

HRID 2092959 reaction equation
[NH2:1][C@@H:2]([CH:5]([CH2:8][CH3:9])[CH2:6][CH3:7])[CH2:3][OH:4].[Cl:10][C:11]1[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=1>CCN(CC)CC>[Cl:10][C:11]1[S:15][C:14]([S:16]([NH:1][C@H:2]([CH2:3][OH:4])[CH:5]([CH2:8][CH3:9])[CH2:6][CH3:7])(=[O:18])=[O:17])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 10192571HCID 10192571, compound

Product 1

HCID 11358855GSI-136Yield 91%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Accordingly, the intermediate (S)-2-amino-3-ethyl pentan-1-ol (9) is condensed with 5-chlorothiophene-2-sulfonyl chloride in the presence of Et3N to obtain (S)—N-(5-chlorothiophene-2-sulfonyl)-β,β-diethylalaninol, in 91% yield and 98% ee (determined by chiral HPLC).

Sources & evidence

ORD record
ord-64851b9784154605a4c6919e0fcbf3b5
Source dataset
uspto-grants-2013_05
Patent number
US08440844B2

Reaction notes

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