Triethylamine → GSI-136

HRID 2092960Notes

Reaction equation

HRID 2092960 reaction equation
[NH2:1][C@@H:2]([CH:5]([CH2:8][CH3:9])[CH2:6][CH3:7])[CH2:3][OH:4].C(N(CC)CC)C.[Cl:17][C:18]1[S:22][C:21]([S:23](Cl)(=[O:25])=[O:24])=[CH:20][CH:19]=1>C(Cl)Cl>[Cl:17][C:18]1[S:22][C:21]([S:23]([NH:1][C@H:2]([CH2:3][OH:4])[CH:5]([CH2:8][CH3:9])[CH2:6][CH3:7])(=[O:25])=[O:24])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 10192571HCID 10192571, compound

Product 1

HCID 11358855GSI-136Yield 45.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of (S)-2-amino 3ethyl pentan-1-ol (9) (200 mg) and methylene chloride (20 mL) was placed under argon, and cooled to 0° C. Triethyl amine (484 mg) was added followed by the drop wise addition of 5-chlorothiophene-2-sulfonyl chloride (347.2) in methylene chloride (5 mL) for 30 min to obtain (S)—N-(5-chlorothiophene-2-sulfonyl)-β,β-diethylalaninol (1A) (45.2% overall yield and 98% ee).

Sources & evidence

ORD record
ord-e20e7c65b249456e93ed6852eb79668e
Source dataset
uspto-grants-2013_05
Patent number
US08440844B2

Reaction notes

Loading…