2,2-Dimethylpropyl carbonochloridate → (3R,4R)-1-Neopentyloxycarbonyl-4-phenyl-3-triethylsilyloxy-azetidin-2-one

HRID 895815Notes

Reaction equation

HRID 895815 reaction equation
[CH2:1]([O:6][C:7](Cl)=[O:8])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:10]1([C@H:16]2[NH:19][C:18](=[O:20])[C@@H:17]2[O:21][Si:22]([CH2:27][CH3:28])([CH2:25][CH3:26])[CH2:23][CH3:24])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:1]([O:6][C:7]([N:19]1[C@H:16]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@@H:17]([O:21][Si:22]([CH2:27][CH3:28])([CH2:25][CH3:26])[CH2:23][CH3:24])[C:18]1=[O:20])=[O:8])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 33521852,2-Dimethylpropyl carbonochloridateHCID 60147326HCID 60147326, compound

Product 1

HCID 69742751(3R,4R)-1-Neopentyloxycarbonyl-4-phenyl-3-triethylsilyloxy-azetidin-2-one

Procedure

By following the above procedure and using neopentylchloroformate, (3R,4R)-4-phenyl-3-triethylsilyloxy-azetidin-2-one was converted to the title product: 1H NMR (CDCl3) δ 0.39-0.97 (m, 24H), 3.73 (d, 1H, J=10.2 Hz), 3.90 (d, 1H, J=10.2 Hz), 5.10 (m, 2H), 7.31 (m, 5H).

Sources & evidence

ORD record
ord-5e6d434b6aeb4192aa808a7d1a6cda84
Source dataset
uspto-grants-2005_07
Patent number
US06916942B2

Reaction notes

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