Bromine → HCID 15871326, compound

HRID 367231Notes

Reaction equation

HRID 367231 reaction equation
C(C(NC(C1C=C(F)C=CC=1S[S:20][N:21]([C:30](=[O:38])[C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][CH:32]=1)[CH:22]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:23]([OH:25])=[O:24])=O)CC(C)C)(O)=O.BrBr>C(#N)C.ClCCl>[CH3:28][CH:27]([CH3:29])[CH2:26][C@H:22]([N:21]1[C:30](=[O:38])[C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[S:20]1)[C:23]([OH:25])=[O:24]

Participants

5

Reactant 2

HCID 24408BromineHCID 765083782-[-[2-(1-Carboxy-3-methyl-butylcarbamoyl)-4-fluorophenyldisulfanyl]-5-fluorobenzoylamino]-4-methyl-pentanoic acid

Product 1

HCID 15871326HCID 15871326, compoundYield 137.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

Following the general method of Example 3, a slurry of {s-(R*,R*)]-2-{-[2-(1-carboxy-3-methyl-butylcarbamoyl)-4-fluorophenyldisulfanyl]-5-fluorobenzoylamino}-4-methyl-pentanoic acid (2.1 g, 3.6 mmol) (from Preparation 21) in 8 mL acetonitrile and 25 mL dichloromethane was treated with bromine (0.7 g, 4.4 mmol) in 15 mL dichloromethane. The crude compound was recrystallized from methanol/water to afford 1.4 g of the title compound, mp 161-162° C.

Workup

  1. customThe crude compound was recrystallized from methanol/water

Sources & evidence

ORD record
ord-018ed6bc8c5f4ff4bb1d0be194566a6c
Source dataset
uspto-grants-2000_10
Patent number
US06133270

Reaction notes

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