Benzyl Alcohol → Methyl 5-[(4-methyl-1-piperazinyl)sulfonyl]-2-[(phenylmethyl)oxy]benzoate

HRID 1623693Notes

Reaction equation

CCOC(/N=N/C(OCC)=O)=O.[OH:13][C:14]1[CH:23]=[CH:22][C:21]([S:24]([N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)(=[O:26])=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:53]1([CH2:59]O)[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>C1(C)C=CC=CC=1.CCOCC>[CH3:33][N:30]1[CH2:29][CH2:28][N:27]([S:24]([C:21]2[CH:22]=[CH:23][C:14]([O:13][CH2:59][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[C:15]([CH:20]=2)[C:16]([O:18][CH3:19])=[O:17])(=[O:26])=[O:25])[CH2:32][CH2:31]1

Participants

Conditions

Temperature: 0 °C

Procedure

DEAD (0.24 ml, 1.51 mmol) was slowly added to a mixture of methyl 2-hydroxy-5-[(4-methyl-1-piperazinyl)sulfonyl]benzoate (may be prepared as described in Description 70; 430 mg, 1.37 mmol), Ph3P (395 mg, 1.51 mmol) and phenylmethanol (163 mg, 1.505 mmol) in toluene (15 ml) cooled in an ice bath at 0° C. The mixture was stirred for 2 h at room temperature. Ether was added to the mixture and the mixture was filtered. The filtrate was evaporated to yield the title compound. 260 mg.

Workup

filtrationthe mixture was filtered
customThe filtrate was evaporated

Sources & evidence

ORD record: ord-7b1f08e22e934ecaaa1c22553a55d52a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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