tert-butyl N-(prop-2-yn-1-yl)carbamate → HCID 130217018, compound

HRID 1424517Notes

Reaction equation

HRID 1424517 reaction equation
[CH2:1]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:2]#[CH:3].[CH2:12]([O:19][N:20]1[C:26](=[O:27])[N:25]2[CH2:28][C@H:21]1[CH2:22][CH2:23][C@H:24]2[C:29](Cl)=[N:30][OH:31])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl.CCOC(C)=O>[C:7]([O:6][C:5](=[O:11])[NH:4][CH2:1][C:2]1[O:31][N:30]=[C:29]([C@@H:24]2[CH2:23][CH2:22][C@@H:21]3[CH2:28][N:25]2[C:26](=[O:27])[N:20]3[O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1)([CH3:8])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 86701375HCID 86701375, compound

Product 1

HCID 130217018HCID 130217018, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl prop-2-yn-1-ylcarbamate (0.37 g, 2.4 mmol) was added to the solution of (2S,5R)-6-(benzyloxy)-N-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbimidoyl chloride (˜2.0 mmol) in dry DCM (20 mL), followed by the addition of TEA (0.31 mL, 2.2 mmol) in dry DCM (2.0 mL) over a period of 30 minutes. The reaction mixture was stirred at rt overnight, then the mixture was diluted with EtOAc, washed with water and saturated sodium chloride. The organic layer was dried over Na2SO4, concentrated and purified by silica gel column chromatography (1:2 petroleum ether/EtOAc) to afford tert-butyl((3-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)isoxazol-5-yl)methyl)carbamate (180 mg, 21% for two steps) as a white solid. ESI-MS (EI+, m/z): 429.1 [M+H]+. 1H NMR (500 MHz, CDCl3): δ 7.45-7.35 (m, 5H), 6.24 (s, 1H), 5.09 (d, J=11.5 Hz, 1H), 4.93 (d, J=11.5 Hz, 1H), 4.58 (d, J=7.5 Hz, 1H), 4.43 (m, 2H), 3.32 (s, 1H), 2.86-2.84 (m, 1H), 2.68 (d, J=11.5 Hz, 1H), 2.34-2.30 (m, 1H), 2.23-2.18 (m, 1H), 2.10-2.04 (m, 1H), 1.82-1.78 (m, 1H), 1.45 (s, 9H).

Workup

  1. washwashed with water and saturated sodium chloride
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (1:2 petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-62240805872c441a99b1bc0b77d43eb3
Source dataset
uspto-grants-2015_01
Patent number
US08927724B2

Reaction notes

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