Phthalic Anhydride → HCID 178445896, compound

HRID 1396956Notes

Reaction equation

HRID 1396956 reaction equation
[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:40][CH2:41][CH2:42][CH3:43])[C:14]([N:16]1[C@H:20]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[O:22])[CH2:19][CH2:18][N:17]1[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])=[O:15])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:2].C(N)(N)=[O:45].OO.C1(=O)C2C=CC=CC=2C(=O)O1>CCOC(C)=O>[CH:1]([N:3]([CH2:12][C@@H:13]([CH2:40][CH2:41][CH2:42][CH3:43])[C:14]([N:16]1[C@H:20]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N+:25]=2[O-:45])=[O:22])[CH2:19][CH2:18][N:17]1[C:30]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:31])=[O:15])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:2]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 31294Carbamide PeroxideHCID 86706388Phenylmethyl (3S)-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)hexanoyl]-3-[(2-pyridinylamino)carbonyl]-1-pyrazolidinecarboxylate

Product 1

HCID 178445896HCID 178445896, compoundYield 118.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of phenylmethyl (3S)-2-[(2R)-2-({formyl [(phenylmethyl)oxy]amino}methyl)hexanoyl]-3-[(2-pyridinylamino)carbonyl]-1-pyrazolidinecarboxylate (70 mg, 0.12 mmol) in EtOAc (6 mL) was added per carbamide (45 mg, 0.48 mmol) and 2-benzofuran-1,3-dione (71 mg, 0.48 mmol). The mixture was stirred overnight until TLC showed the completion of the reaction. The mixture was washed with aq. Na2CO3 and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography to provide the titled compound (86 mg, 85%)

Workup

  1. customthe completion of the reaction
  2. washThe mixture was washed with aq. Na2CO3 and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-7f7e11c52fc646329ff9a5cf86dff1f2
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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