Acetic Acid → tert-butyl 2-((2S,5R)-6-(benzyloxy)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate

HRID 627239Notes

Reaction equation

HRID 627239 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]([OH:29])(=[O:28])C.CCN([CH:36]([CH3:38])[CH3:37])C(C)C.[CH2:39](O)C>C(Cl)Cl.[Zn]>[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][NH:23][C:26](=[O:28])[O:29][C:36]([CH3:38])([CH3:39])[CH3:37])=[CH:12][C@H:13]2[C:18](=[O:19])[NH2:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 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 89852204tert-butyl 2-((2S,5R)-6-(benzyloxy)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamateYield 61%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

(2S,5R)-6-(benzyloxy)-4-(2-nitroethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide (Intermediate 226, 0.420 g, 1.21 mmol) was taken up in ethanol (absolute, 99.5%) (20 mL), and zinc dust (1.983 g, 30.32 mmol) was added followed by acetic acid (2.78 mL, 48.51 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. DIPEA (2.118 mL, 12.13 mmol) was added followed by BOC-anhydride (0.845 mL, 3.64 mmol). The reaction mixture was stirred for 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 2 hours
  2. washwashed with saturated bicarbonate
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-347e8cf6c43c4901a12622b230be4c2d
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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