Ethyl Acetate → HCID 178452375, compound

HRID 2289054Notes

Reaction equation

HRID 2289054 reaction equation
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([CH2:8][O:9][C:10]([N:12]=[C:13]([NH:19][C:20](=[O:32])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)N2C=CC=N2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:35][CH2:36][C:37]([NH:39][CH:40]1[CH2:43][N:42]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:41]1)=[O:38].C(OCC)(=O)C>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]=[C:13]([NH:19][C:20]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:32])[NH:35][CH2:36][C:37]([NH:39][CH:40]2[CH2:43][N:42]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:41]2)=[O:38])=[O:11])=[CH:33][CH:34]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 18699815Tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylateHCID 54574361HCID 54574361, compound

Product 1

HCID 178452375HCID 178452375, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under ice cooling, a solution of 4-nitrobenzyl [(4-nitrobenzyloxy)carbonyliminopyrazol-1-ylmethyl]carbamate (1.42 g) in tetrahydrofuran (12 ml) was added to a solution of tert-butyl 3-(aminoacetylamino)-1-azetidinecarboxylate (785 mg) in tetrahydrofuran (13 ml) and the mixture was stirred at room temperature for 3 hours. Ethyl acetate was added to the reaction mixture. The resulting mixture was washed with water, an aqueous solution of potassium hydrogensulfate and saturated saline, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was crystallized from diisopropyl ether, followed by washing, whereby 1.94 g of the title compound were obtained as a colorless crystals.

Workup

  1. washThe resulting mixture was washed with water
  2. dry with materialan aqueous solution of potassium hydrogensulfate and saturated saline, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customThe residue was crystallized from diisopropyl ether
  5. washby washing

Sources & evidence

ORD record
ord-1e55bd4abc8d44cc8cb873cd09d7b743
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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