Acetonitrile → HCID 69962025, compound

HRID 367232Notes

Reaction equation

HRID 367232 reaction equation
C(C(NC(C1C=C(C)C=CC=1S[S:20][N:21]([C:30](=[O:38])[C:31]1[CH:36]=[C:35](C)[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:41](#N)C>ClCCl>[CH3:29][CH:27]([CH3:28])[CH2:26][C@H:22]([N:21]1[C:30](=[O:38])[C:31]2[CH:32]=[CH:33][C:34]([CH3:41])=[CH:35][C:36]=2[S:20]1)[C:23]([OH:25])=[O:24]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24408BromineHCID 76485927HCID 76485927, compound

Product 1

HCID 69962025HCID 69962025, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Following the general method of Example 3, a slurry of [s-(R*,R*)]-2-[-[2-(1-carboxy-3-methyl-butylcarbamoyl)-4-methylphenyldisulfanyl]-5-methylbenzoylamino]-4-methyl-pentanoic acid (1.8 g, 3.2 mmol) (from Preparation 22) in 5 mL acetonitrile and 20 mL dichloromethane was reacted with bromine (0.6 g, 3.7 mmol) in 10 mL dichloromethane. The crude product was recrystallized from methanol/water to afford 1.3 g of the title compound.

Workup

  1. customThe crude product was recrystallized from methanol/water

Sources & evidence

ORD record
ord-a0062990754647b6b6cd21480c854a4a
Source dataset
uspto-grants-2000_10
Patent number
US06133270

Reaction notes

Loading…