Chlorosuccinimide → HCID 86701371, compound

HRID 515595Notes

Reaction equation

HRID 515595 reaction equation
C1C(=O)N(Cl)C(=O)C1.[CH2:9]([O:16][N:17]1[C:23](=[O:24])[N:22]2[CH2:25][CH:18]1[CH2:19][CH2:20][CH:21]2/[CH:26]=[N:27]/[OH:28])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:29]([Si:31]([CH3:34])([CH3:33])[CH3:32])#[CH:30].CCN(C(C)C)C(C)C>N1C=CC=CC=1.C(Cl)Cl>[CH2:9]([O:16][N:17]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:18]1[CH2:19][CH2:20][C@H:21]2[C:26]1[CH:30]=[C:29]([Si:31]([CH3:34])([CH3:33])[CH3:32])[O:28][N:27]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 31398ChlorosuccinimideHCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 898717762-[(E)-hydroxyiminomethyl]-6-phenylmethoxy-1,6-diazabicyclo[3.2.1]octan-7-one

Product 1

HCID 86701371HCID 86701371, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

NCS (290 mg, 2.17 mmol) and pyridine (2 drops) were added to a solution of (E)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbaldehyde oxime (560 mg, 2.04 mmol) in dry DCM (15 mL). The reaction mixture was stirred at rt for about 3-4 hrs. Ethynyltrimethylsilane (240 mg, 2.44 mmol) was added, then a solution of DIPEA (290 mg, 2.24 mmol) in dry DCM (5 mL) was added slowly over a 0.5 h period. After addition, the reaction mixture was stirred at rt overnight. The reaction mixture was then washed with 10% citric acid, water, saturated sodium chloride (10 mL), dried and concentrated. The residue was purified by silica gel column chromatography (10:1 petroleum ether/EtOAc) to afford (2S,5R)-6-(benzyloxy)-2-(5-(trimethylsilyl)isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (300 mg, 41%) as a colorless oil. ESI-MS (EI+, m/z): 372 [M+H]+.

Workup

  1. additionAfter addition
  2. stirringthe reaction mixture was stirred at rt overnight
  3. washThe reaction mixture was then washed with 10% citric acid, water, saturated sodium chloride (10 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (10:1 petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-e904ec5a2f6a47d3a80abf1112fe1c06
Source dataset
uspto-grants-2015_08
Patent number
US09108966B2

Reaction notes

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