Trimethyl orthoacetate → HCID 68505210, compound

HRID 1508392Notes

Reaction equation

[Si:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2([CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[N:19]([C:20]([NH:22][NH2:23])=[S:21])[N:18]=[C:17]([C:24]3[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=3[F:31])[S:16]2)[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO[C:45](OC)(OC)[CH3:46]>CC1C=CC(S(O)(=O)=O)=CC=1>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2([CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[N:19]([C:20]3[S:21][C:45]([CH3:46])=[N:23][N:22]=3)[N:18]=[C:17]([C:24]3[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=3[F:31])[S:16]2)[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Tert-butyl 3-(2-(3-(tert-butyldimethylsilyloxy)phenyl)-5-(2,5-difluorophenyl)-3-(hydrazinecarbonothioyl)-2,3-dihydro-1,3,4-thiadiazol-2-yl)propylcarbamate (100 mg, 0.157 mmol) was weighed into a 25 mL flask and suspended in 5.0 mL of 1,1,1-trimethoxyethane (5 mL, 0.157 mmol). 4-methylbenzenesulfonic acid (0.540 mg, 0.00314 mmol) was then added, and the reaction heated to 80° C. for 1 hour. The reaction mixture was concentrated in vacuo, and the residue was purified by flash column chromatography (20-50% ethyl acetate/hexanes), to afford 75 mg (72% yield) of the desired product as a yellow solid on standing.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe residue was purified by flash column chromatography (20-50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-faef69d3a64b4acb88bebe60a0cd2462
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221841B2

Reaction notes

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