Ethyl Acetate → HCID 178452035, compound

HRID 2289080Notes

Reaction equation

HRID 2289080 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)=[O:4].[N+:18]([C:21]1[CH:51]=[CH:50][C:24]([CH2:25][O:26][C:27]([N:29]=[C:30]([NH:36][C:37](=[O:49])[O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=2)N2C=CC=N2)=[O:28])=[CH:23][CH:22]=1)([O-:20])=[O:19].C(OCC)(=O)C>O1CCCC1>[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([CH2:25][O:26][C:27]([N:29]=[C:30]([NH:36][C:37]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=2)=[O:49])[NH:1][CH2:2][C:3]([NH:5][C@H:6]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]2)=[O:4])=[O:28])=[CH:50][CH:51]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 118068461,1-Dimethylethyl (3S)-3-[(2-aminoacetyl)amino]-1-pyrrolidinecarboxylateHCID 54574361HCID 54574361, compound

Product 1

HCID 178452035HCID 178452035, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (3S)-3-(2-aminoacetylamino)-1-pyrrolidinecarboxylate (3.07 g) in anhydrous tetrahydrofuran (45 ml), a solution of 4-nitrobenzyl [(4-nitrobenzyloxy)carbonylimino-pyrazol-1-ylmethyl]carbamate (5.38 g) in tetrahydrofuran (35 ml) was added under ice cooling, followed by stirring at room temperature for 30 minutes. 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 then concentrated by evaporation under reduced pressure. The residue was purified by chromatography through a silica gel column (ethyl acetate-dichloromethane), whereby the title compound (7.82 g) was obtained as an amorphous substance.

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 purified by chromatography through a silica gel column (ethyl acetate-dichloromethane), whereby the title compound (7.82 g)
  5. customwas obtained as an amorphous substance

Sources & evidence

ORD record
ord-9224c338b92d40ca968459ea370a3e59
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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