Lithium Bromide → HCID 59854765, compound

HRID 2112779Notes

Reaction equation

HRID 2112779 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:18][CH:17]([CH2:19][CH2:20][CH2:21][CH3:22])[CH:16](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]=[C:17]([CH2:19][CH2:20][CH2:21][CH3:22])[CH:16]=[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

3

Reactant 2

HCID 82050Lithium BromideHCID 59854740HCID 59854740, compound

Product 1

HCID 59854765HCID 59854765, compoundYield 18.3%

Procedure

Compound 03-5 (4.54 g, 10.9 mmol) was converted with LiBr (1.04 g, 12 mmol, 1.1 equiv.), Li2CO3 (886 mg, 12 mmol, 1.1 equiv.) to 03-6 using the procedure for 01-6. The crude product was washed with EtOAc (15 mL) and washed with Et2O (2×15 mL) to give 03-6 (1.8 g, 5.4 mmol 49%) as a brownish solid. The mother liquor was evaporated and treated with Et2O to give a second crop of 03-6 (0.67 g, 2.0 mmol, 18%) as a brownish solid. Total yield of 03-6: 2.47 9, 7.4 mmol, 68%.

Workup

  1. washThe crude product was washed with EtOAc (15 mL)
  2. washwashed with Et2O (2×15 mL)
  3. customto give 03-6 (1.8 g, 5.4 mmol 49%) as a brownish solid
  4. customThe mother liquor was evaporated
  5. additiontreated with Et2O

Sources & evidence

ORD record
ord-2ae9687aba824a3ba344f4bc774b283a
Source dataset
uspto-grants-2009_04
Patent number
US07524853B2

Reaction notes

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