Dimethylformamide → HCID 86693977, compound

HRID 330954Notes

Reaction equation

HRID 330954 reaction equation
[O:1]=[C:2]1[N:8]2[CH2:9][C@@H:4]([CH2:5][CH2:6][C@H:7]2[C:10]([NH:12][O:13][C@H:14]2[CH2:18][CH2:17][NH:16][CH2:15]2)=[O:11])[N:3]1[O:19]S(O)(=O)=O.C(OC(OC(O[C:34]1[CH:39]=[CH:38][C:37]([N+]([O-])=O)=[CH:36][CH:35]=1)=O)C)(=O)C.[CH2:43]([N:45](CC)CC)C.[CH3:50]N(C)C=O>C(Cl)Cl>[CH2:50]([O:19][N:3]1[C:2](=[O:1])[N:8]2[CH2:9][C@H:4]1[CH2:5][CH2:6][C@H:7]2[C:10]([NH:12][O:13][CH2:14][C:18]1[N:45]([CH3:43])[CH:15]=[N:16][CH:17]=1)=[O:11])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 117805601-acetoxyethyl p-nitrophenyl carbonateHCID 71714408(2S,5R)-7-oxo-N-[(3S)-pyrrolidin-3-yloxy]-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Product 1

HCID 86693977HCID 86693977, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2S,5R)-7-oxo-N-[(3S)-pyrrolidin-3-yloxy]-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide Compound 2 (Table 1) (0.030 g, 0.086 mmol, Example 2) in DMF (dimethyl formamide) (1.5 mL) was added 1-{[(4-nitrophenoxy)carbonyl]oxy}ethyl acetate 103 (0.027 g, 0.102 mmol, J. Med. Chem., 1988, vol 31, 2, p 318-322) and triethylamine (0.023 mL, 0.171 mmol) sequentially at room temperature. The mixture was stirred at room temperature overnight, diluted with DCM and concentrated to provide a residue, which was subjected to chromatography and preparative HPLC to give Compound 101 (Table 1) (0.011 g) as a white solid.

Workup

  1. concentrationconcentrated
  2. customto provide a residue, which

Sources & evidence

ORD record
ord-958b6c1f1d8c408caf670ba4384722fd
Source dataset
uspto-grants-2014_11
Patent number
US08877743B2

Reaction notes

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