Lithium Bromide → HCID 68867386, compound

HRID 2112784Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:18][CH2:17][C:16]([CH2:20][CH2:21][CH2:22][CH3:23])(Br)[C:15](=[O:24])[C:8]=2[S:9][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])=[O:5])[CH3:2].[Li+].[Br-]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:18]=[CH:17][C:16]([CH2:20][CH2:21][CH2:22][CH3:23])=[C:15]([OH:24])[C:8]=2[S:9][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])=[O:5])[CH3:2]

Participants

Reactant 2

HCID 82050Lithium Bromide

HCID 68864998HCID 68864998, compound

Product 1

HCID 68867386HCID 68867386, compoundYield 52.3%

Procedure

Compound 04-5 (4.74 g, 10.9 mmol) was converted with LiBr (1.1 g, 12.5 mmol, 1.1 equiv.), Li2CO3 (0.9 g, 12.5 mmol, 1.1 equiv.) to 04-6 using the procedure for 02-6. The crude product was filtered off after aqueous workup, washed with H2O and Et2O (25 mL) to give 04-6 (1.9 g, 5.7 mmol, 50%) as a grey solid. The mother liquor was evaporated and treated with Et2O to give a second crop of 04-6 (0.6 g, 1.9 mmol, 17%) as a brownish solid (total yield of 04-6: 2.6 g, 7.6 mmol, 67%).

Workup

filtrationThe crude product was filtered off after aqueous workup
washwashed with H2O and Et2O (25 mL)

Sources & evidence

ORD record: ord-9d635ed824a645c783aaf64d9c64a6c7
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524853B2

Reaction notes

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