p-Toluenesulfonic acid → HCID 22850604, compound

HRID 485998Notes

Reaction equation

[F:1][C@@H:2]([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C@@H:20]([O:26]C3CCCCO3)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:14][CH:13]=2)=[N:10][CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CO>[F:1][C@@H:2]([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C@@H:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:14][CH:13]=2)=[N:8][CH:7]=1

Participants

Conditions

Temperature: 5 °C

Procedure

In a reaction flask were charged 6.4 g of the compound obtained in step 1 and 485 ml of methanol, followed by cooling to 5° C. A solution of 0.805 g of p-toluenesulfonic acid (monohydrate) in 201.5 ml of methanol was added thereto dropwise at that temperature over 1 hour. After the addition, the reaction temperature was elevated to 20° C., and the mixture was stirred at that temperature until the reaction completed while monitoring the unreacted substance by HPLC. After completion of the reaction, the reaction mixture was neutralized with a sodium hydrogencarbonate aqueous solution, and methanol was removed by distillation under reduced pressure to obtain 7.0 g of a crude product. Purification by silica gel column chromatography furnished 2.87 g of the titled compound.

Workup

additionAfter the addition
customwas elevated to 20° C.
customAfter completion of the reaction
customwas removed by distillation under reduced pressure
customto obtain 7.0 g of a crude product
customPurification by silica gel column chromatography

Sources & evidence

ORD record: ord-b2afbb4345ef4b9db535cafdc2d82c2a
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05290477

Reaction notes

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