Hexane → HCID 11538914, compound

HRID 1713041Notes

Reaction equation

C([O:3][C:4](=[O:30])[CH2:5][CH2:6][CH2:7][N:8]1[C:27](=[S:28])[N:11]2[C:12]3[CH:13]=[C:14]([C:18]4[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=4)[S:15][C:16]=3[CH:17]=[C:10]2[C:9]1=[O:29])C.CCCCCC>C(O)(C(F)(F)F)=O.O.C(OCC)(=O)C>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([C:14]2[S:15][C:16]3[CH:17]=[C:10]4[C:9](=[O:29])[N:8]([CH2:7][CH2:6][CH2:5][C:4]([OH:30])=[O:3])[C:27](=[S:28])[N:11]4[C:12]=3[CH:13]=2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

Conditions

Temperature: 70 °C

Procedure

Compound 31 (20 mg, 0.046 mmol) was dissolved in a mixture of TFA and water (4:1, 2 ml) and the resulting solution was heated at 70° C. for 5 hours, while monitoring the reaction progress by TLC using a 6:4 hexane:ethyl acetate mixture as eluent. The mixture was cooled to room temperature and left intact for one hour. The formed precipitate was thereafter filtered and washed with small portions of ethanol. The crude residue was recrystallized from ethanol to give pure Compound 32 (10 mg, 56% yield).

Workup

temperatureThe mixture was cooled to room temperature
filtrationThe formed precipitate was thereafter filtered
washwashed with small portions of ethanol
customThe crude residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-d90252928db241f3a59bce3ec71e900a
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795255B2

Reaction notes

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