Benzenesulfonic Acid → HCID 86611562, compound

HRID 1909701Notes

Reaction equation

HRID 1909701 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:27]=[CH:26][C:12]([O:13][CH2:14][C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[C:28]1([S:34]([OH:37])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CCOCC>[C:28]1([S:34]([OH:37])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:27]=[CH:26][C:12]([O:13][CH2:14][C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7371Benzenesulfonic AcidHCID 44537807DG 051 (free base)

Product 1

HCID 86611562HCID 86611562, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

500 mg of 4-{(S)-2-[4-(4-chloro-phenyoxy)-phenoxymethyl]-pyrrolidin-1-yl}-butyric acid was dissolved in ether (120 ml). To the solution was added dropwise the solution of benzensulfonic acid (240 mg, 1.2 eq.) in ether (4 ml). The mixture was stirred at rt for 2 h. Ether was removed to about 50 ml. The white solid was collected by filtration and washed with ether and dried on a vacuum line at 70° C. over weekend to provide the title product (595 mg, 63%); 1H NMR (400 MHz, DMSO-d6) δ 1.80˜2.05 (m, 5H), 2.25 (m, 1H), 2.37 (t, J=7.2 Hz, 2H), 3.17 (m, 2H), 3.44 (m, 1H), 3.62 (m, 1H), 3.94 (m, 1H), 4.15 (t, J=8.4 HZ, 1H), 4.30 (dd, J=3.2, 10.8 Hz, 1H), 6.94 (d, J=9.2 Hz, 2H), 7.06 (s, 4H), 7.31 (m, 3H), 7.41 (d, J=9.2 Hz, 2H), 7.60 (m, 2H). HPLC purity: 99%; MS?

Workup

  1. customEther was removed to about 50 ml
  2. filtrationThe white solid was collected by filtration
  3. washwashed with ether
  4. customdried on a vacuum line at 70° C. over weekend

Sources & evidence

ORD record
ord-f7152bb2b70a4cb091a6983ced409b00
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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