Hydrogen Bromide → HCID 20586041, compound

HRID 1977461Notes

Reaction equation

HRID 1977461 reaction equation
[C:1]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][CH:14]([CH3:16])[CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN1CC[O:24][CH2:23][CH2:22]1.ClC(OCC(C)C)=O.[BrH:35]>C1COCC1>[Br:35][CH2:22][C:23]([C:17](=[O:19])[C@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])=[O:24]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 74840Leucine, N-carboxy-, N-benzyl ester, L-

Product 1

HCID 20586041HCID 20586041, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

N-Cbz-L-leucine (2.10 g, 7.6 mmol) was dissolved in THF (10 mL), cooled to −40° C., and 4-methylmorpholine (0.77 g, 7.6 mmol, 0.83 mL) was added, followed by dropwise addition of isobutyl chloroformate (1.04 g, 7.6 mmol, 0.98 mL). After 15 min, the solution was filtered into the previously prepared 0° C. solution of ethereal diazomethane. The resulting solution was allowed to stand at 0° C. for 23 h. HBr (30% in acetic acid) (45.2 mmol, 9 mL) was added and the resulting solution was stirred at 0° C. for 5 min, then washed sequentially with 0.1 N HCl, saturated aqueous NaHCO3 and saturated brine, then dried (MgSO4), filtered and concentrated to give the title compound as a colorless oil (2.43 g, 94%).

Workup

  1. filtrationthe solution was filtered into the previously prepared 0° C. solution of ethereal diazomethane
  2. waitto stand at 0° C. for 23 h
  3. washwashed sequentially with 0.1 N HCl, saturated aqueous NaHCO3 and saturated brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-df5c6b58579d4412b3d09ac9d3d10ff1
Source dataset
uspto-grants-2001_05
Patent number
US06232342B1

Reaction notes

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