2-Fluorobenzenesulphonyl chloride → HCID 59054573, compound

HRID 1479925Notes

Reaction equation

HRID 1479925 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])(=[O:10])=[O:9].[F:24]C1C=CC=CC=1S(Cl)(=O)=O>>[F:24][C:7]1[CH:2]=[C:3]([S:8]([NH:11][C@H:12]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:13]([OH:15])=[O:14])(=[O:10])=[O:9])[CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 1377612-Fluorobenzenesulphonyl chlorideHCID 59054575HCID 59054575, compound

Product 1

HCID 59054573HCID 59054573, compound

Procedure

Following 17a synthetic method, using 2-fluorobenzenesulfonyl chloride (145.62 μL, 1.1 mmol) instead of 2-fluorobenzenesulfonyl chloride gave the final compound 18a as a colorless oil; (77.34 mg, 45.6%). [α]D25: +21.3 (c=0.25, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 7.95-7.76 (m, 3H), 7.41-7.25 (m, 6H), 5.04-4.97 (m, 1H), 3.45-2.26 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.50, 163.90, 160.62, 139.15, 136.64, 133.50, 129.49, 128.40, 126.89, 124.94, 118.56, 115.15, 109.30, 54.04, 36.79; HRMS (ESI): calcd for: C15H14FNO5S [M+Na]+=362.0469, obsd [M+Na]+=362.0475.

Sources & evidence

ORD record
ord-b86cf7eb92d5457893b7548eca113293
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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