Diiodomethane → HCID 67170489, compound

HRID 1918291Notes

Reaction equation

C[O:2][C:3]([C:5]1([NH:12][C:13](=[O:32])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH2:24][C:25]3[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=3)[CH:15]=2)[CH2:10][CH2:9][C:8](=[CH2:11])[CH2:7][CH2:6]1)=[O:4].[CH2:33]([Zn]CC)C.ICI>C1(C)C=CC=CC=1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([NH:12][C:5]2([C:3]([OH:2])=[O:4])[CH2:6][CH2:7][C:8]3([CH2:33][CH2:11]3)[CH2:9][CH2:10]2)=[O:32])=[CH:15][C:16]=1[O:22][CH2:23][CH2:24][C:25]1[CH:26]=[C:27]([CH3:31])[CH:28]=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The compound of step 1 of example 56 (400 mg, 0.91 mmol) was dissolved in toluene (8 ml) and diethylzinc (2.7 ml, 2.7 mmol, solution in hexane) was added. The mixture was heated to 60° C. and diiodomethane (1.10 g, 4.11 mmol) was added with stirring. This mixture was reacted at 60° C. overnight, the addition of diethyl zinc and diiodomethane was repeated and stirring continued for another night. The mixture was partitioned between EA and 2 N hydrochloric acid, the aqueous phase was extracted with EA, the combined organic phases were washed with aqueous sodium hydrogencarbonate solution, dried over sodium sulfate and evaporated to dryness. The obtained methyl ester was hydrolyzed in analogy to step 4 of example 1 to yield the title compound (15 mg).

Workup

customThis mixture was reacted at 60° C. overnight
stirringstirring
waitcontinued for another night
customThe mixture was partitioned between EA and 2 N hydrochloric acid
extractionthe aqueous phase was extracted with EA
washthe combined organic phases were washed with aqueous sodium hydrogencarbonate solution
dry with materialdried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-471d685f5843473d8f62f070e7f3efb2
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618304B2

Reaction notes

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