1-Hydroxybenzotriazole → Carbamate

HRID 1108026Notes

Reaction equation

HRID 1108026 reaction equation
C1C=C[C:4]2N(O)N=N[C:5]=2[CH:6]=1.[CH3:11][C:12]([O:15][C:16]([NH:18][C@@H](C(O)=O)C1C=CC=CC=1)=[O:17])(C)[CH3:13].C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:15]([CH:5]([CH3:4])[CH3:6])[CH:12]([CH3:13])[CH3:11].[C:16](=[O:15])([O-:17])[NH2:18]

Participants

6

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 2755953(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid

Product 2

HCID 276CarbamateYield 494.7%HCID 7914Diisopropyl Ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Dissolve the product of Step 2 (134 g) in CH2Cl2 (1.5 L). Treat sequentially with HOBT (44.6 g), BOC-D-phenylglycine (86.3 g) and DEC (65.9 g). Stir the mixture at 23° C. for 18 h, heat at reflux temperature for 2 h, recool to 23° C., treat with saturated NaHCO3 solution (500 mL), separate the organic portion, dry (MgSO4), filter and concentrate. Recrystallize the crude material, once from Et2O and twice from iPr2O to give 1,1-dimethylethyl-[[[1-[[(3,5-dichlorobenzoyl)methylamine]methyl]-2-(3,4-dichlorophenyl)-5-methyl-hexen-1-ylidene]amino]oxy]-2-oxo-1-phenylethyl]carbamate (51 g). MS(FAB): m/e 722; [α]D 23 =-96.9° (c 0.4 CH2Cl2); m.p. 98-102° C. (dec).

Workup

  1. temperatureheat
  2. temperatureat reflux temperature for 2 h
  3. customseparate the organic portion
  4. dry with materialdry (MgSO4)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customRecrystallize the crude material

Sources & evidence

ORD record
ord-a086271c70814e6ca0a4f9d666f69490
Source dataset
uspto-grants-2000_05
Patent number
US06063926

Reaction notes

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