HCID 21305259, compound → HCID 21305265, compound

HRID 2084532Notes

Reaction equation

HRID 2084532 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[C@H:3]([NH:12][C:13](=[O:29])[C@@H:14]([CH2:19][NH:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:15][CH2:16][CH2:17][CH3:18])[C:4]([C:6]1[N:7]([CH3:11])[CH:8]=[CH:9][N:10]=1)=[O:5].[CH:32](CC(OC(=O)CC=O)=O)=[O:33]>ClCCl>[CH3:31][C:2]([CH3:30])([CH3:1])[C@H:3]([NH:12][C:13](=[O:29])[C@@H:14]([CH2:19][N:20]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:32]=[O:33])[CH2:15][CH2:16][CH2:17][CH3:18])[C:4]([C:6]1[N:7]([CH3:11])[CH:8]=[CH:9][N:10]=1)=[O:5]

Participants

4

Reactant 2

HCID 21305259HCID 21305259, compoundHCID 53941097HCID 53941097, compound

Product 1

HCID 21305265HCID 21305265, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2(R)-[(N-benzyloxyamino)-methyl]-hexanoic acid-[2,2-dimethyl-1(S)-(1-methyl-1H-imidazole-2-carbonyl)-propyl]-amide (77 mg, 0.18 mmol) in dichloromethane (2 mL) at 0° C. was added formylacetic anhydride (50 μL, 0.54 mmol, 3 eqv) and the reaction allowed to stir at room temperature. After 2 hours the solvents were removed in vacuo and the residue azeotroped with toluene (2×30 mL). The product was placed under high vacuum for several hours to give the title compound as an off white waxy solid (76 mg, 93%).

Workup

  1. customAfter 2 hours the solvents were removed in vacuo
  2. customthe residue azeotroped with toluene (2×30 mL)
  3. waitThe product was placed under high vacuum for several hours

Sources & evidence

ORD record
ord-d3e5b93984b547d39c5cfc73ea53b7c1
Source dataset
uspto-grants-2004_04
Patent number
US06716878B1

Reaction notes

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