L-Alaninol → (S)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamide

HRID 1523747Notes

Reaction equation

HRID 1523747 reaction equation
[NH2:1][C@@H:2]([CH3:5])[CH2:3][OH:4].CCN(C(C)C)C(C)C.[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([NH:1][C@@H:2]([CH3:5])[CH2:3][OH:4])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 80307L-AlaninolHCID 81531DiisopropylethylamineHCID 5204032-Bromobenzenesulfonyl chloride

Product 1

HCID 65807018(S)-2-bromo-N-(1-hydroxypropan-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 500 mL round-bottomed flask were added a stirbar, (S)-2-aminopropan-1-ol (2.151 g, 28.65 mmol), dry DCM (100 mL), and DIPEA (14.0 mL, 81.2 mmol). The mixture was then treated with 2-bromobenzene-1-sulfonyl chloride (6.981 g, 27.32 mmol) and stirred for 66.5 hours before concentrating to dryness and subjecting the residue to FCC to give the title compound. (7.31 g, 91%).

Workup

  1. concentrationbefore concentrating to dryness

Sources & evidence

ORD record
ord-b16935c336ae47b096359a1c060b8770
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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