Lithium Bromide → HCID 68593851, compound

HRID 1516619Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH:8]=[C:9]([N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)[C:10]1[CH:32]=[CH:31][C:13]([C:14]([O:16][C@@H:17]([CH2:19]OS(C2C=CC(C)=CC=2)(=O)=O)[CH3:18])=[O:15])=[CH:12][CH:11]=1.[Br-:38].[Li+]>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH:8]=[C:9]([N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)[C:10]1[CH:32]=[CH:31][C:13]([C:14]([O:16][C@@H:17]([CH2:19][Br:38])[CH3:18])=[O:15])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

(2R)-3-{[(4-methylphenyl)sulfonyl]oxy}-2-propyl 4-[imino(pyrrolidin-1-yl)methyl]benzoate trifluoroacetate (45.1 mg, 0.083 mmol) obtained in Step 1 was dissolved in DMF (2 ml), lithium bromide (72 mg, 0.83 mmol) was added thereto, and the mixture was stirred at 50° C. for 2 days. The solvent was evaporated under reduced pressure, and the obtained residue was purified by reversed-phase HPLC in the same manner as in Step 4 of Example 1 to give the title compound.

Workup

customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by reversed-phase HPLC in the same manner as in Step 4 of Example 1

Sources & evidence

ORD record: ord-4fc8186caa5e4fd89e17af703bd8da3f
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227506B2

Reaction notes

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