Acetic Acid → (2S,5R)-4-(2-acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

HRID 627257Notes

Reaction equation

HRID 627257 reaction equation
[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[C:11]([CH2:21][CH2:22][N+:23]([O-])=O)=[CH:12][C@H:13]2[C:18]([NH2:20])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](O)(=[O:28])[CH3:27].CCN(C(C)C)C(C)C.C(OC(=O)C)(=O)C>C(O)C.C(Cl)Cl.[Zn]>[C:26]([NH:23][CH2:22][CH2:21][C:11]1[C@@H:10]2[CH2:17][N:14]([C:15](=[O:16])[N:9]2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:13]([C:18]([NH2:20])=[O:19])[CH:12]=1)(=[O:28])[CH3:27]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 89853135(2S,5R)-6-(benzyloxy)-4-(2-nitroethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide2×

Product 1

HCID 89863102(2S,5R)-4-(2-acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamideYield 99.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,5R)-6-(benzyloxy)-4-(2-nitroethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide (Intermediate 226, 0.300 g, 0.87 mmol) in ethanol (10 mL) was added zinc dust (1.416 g, 21.66 mmol) and acetic acid (1.984 mL, 34.65 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. Then DIPEA (2.118 mL, 12.13 mmol) was added to reaction mixture followed by acetic anhydride (0.245 mL, 2.60 mmol). The reaction mixture was stirred for an additional 2 hours, then diluted with DCM, washed with saturated bicarbonate and concentrated to dryness. Flash chromatography, 0%-10% MeOH/DCM, afforded the title compound as a clear oil (0.31 g, 61%).

Workup

  1. stirringThe reaction mixture was stirred for an additional 2 hours
  2. washwashed with saturated bicarbonate
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8111aa82e42d4b2bab1158e5e0716f91
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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