Acryloyl chloride → HCID 69451735, compound

HRID 1746078Notes

Reaction equation

HRID 1746078 reaction equation
O[CH:2]1[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[Cl:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:3]1=[O:21].[H-].[Na+].[C:24](Cl)(=[O:27])[CH:25]=[CH2:26]>C(Cl)Cl>[C:24]([CH:2]1[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[Cl:12])[N:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:3]1=[O:21])(=[O:27])[CH:25]=[CH2:26]

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 24758Sodium hydrideHCID 694464424-(2-Chlorophenyl)-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one

Product 1

HCID 69451735HCID 69451735, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of C3-hydroxy β-lactam 24 (5.80 g, 19.1 mmol) in 30 ml of freshly distilled CH2Cl2 was added NaH (60% suspension in mineral oil, 0.83 g, 21.0 mmol), and the mixture was stirred for 15 min at room temperature. Acryloyl chloride (2.59 g, 28.64 mmol) was then added dropwise and the resultant mixture was stirred until TLC indicated the disappearance of starting material. The reaction was quenched with a 5% solution of NH4Cl and extracted (3×20 ml) with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4 and purified with column chromatography on silica gel (1:4, EtOAc:hexanes) to give 4.92 g (72%) of 25 as a white solid, mp 99-100° C. 1H NMR (250 MHz) δ 7.33 (d, J=7.9 Hz, 1H), 7.23-7.10 (m, 5H), 6.75 (d, J=8.9 Hz, 2H), 6.17 (d, J=5.0 Hz, 1H), 5.98 (dd, J=16.9, 1.00 Hz, 1H), 5.74 (dd, J=16.9, 10.4 Hz, 1H), 5.69 (d, J=5.0 Hz, 1H), 5.59 (d, J=10.4, 1.0 Hz, 1H), 3.66 (s, 3H). 13C NMR (63 MHz) δ 163.6, 161.2, 156.6, 133.7, 132.3, 130.3, 130.1, 129.8, 128.5, 126.8, 126.5, 118.6, 114.4, 75.3, 61.3, 58.2, 55.3.

Workup

  1. customThe reaction was quenched with a 5% solution of NH4Cl
  2. extractionextracted (3×20 ml) with CH2Cl2
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. custompurified with column chromatography on silica gel (1:4, EtOAc:hexanes)

Sources & evidence

ORD record
ord-7ae16651f165450589a62bae60ec274e
Source dataset
uspto-grants-2015_10
Patent number
US09149440B2

Reaction notes

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