Sodium Hydroxide → HCID 17902137, compound

HRID 2306532Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To 5-sulpho-2,3,3-trimethylindole (potassium salt) (5.0 g, 18 mmol) was added 6-bromohexanoic acid (10.56 g, 53.8 mmol) in 1,2-propanediol (15 ml) and heated at 80° C. for 72 hours. The mixture was cooled and diluted with water (60 ml) and a solution of NaOH (10% in water, 60 ml) with stirring. The product was purified using preparative HPLC (Dynamax, C18 column, gradient of TFA/H2O to TFA/MeCN) to yield a grey/pink solid (2.4 g, 28%).

Workup

temperatureThe mixture was cooled
customThe product was purified

Sources & evidence

ORD record: ord-43c7918e14f74b08ae355deebb5c9d40
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06828116B1

Reaction notes

Loading…