tert-butyl N-[2-(aminooxy)ethyl]-N-methylcarbamate → tert-Butyl{2-[({[(2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}(methyl)carbamate

HRID 710990Notes

Reaction equation

HRID 710990 reaction equation
[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([OH:20])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:25][C:26](=[O:33])[N:27]([CH2:29][CH2:30][O:31][NH2:32])[CH3:28])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26](=[O:33])[N:27]([CH2:29][CH2:30][O:31][NH:32][C:18]([C@@H:13]1[CH2:12][CH2:11][C@@H:10]2[CH2:17][N:14]1[C:15](=[O:16])[N:9]2[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:20])[CH3:28])([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 2

HCID 23398498tert-butyl N-[2-(aminooxy)ethyl]-N-methylcarbamateHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid

Product 1

HCID 72549868tert-Butyl{2-[({[(2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}(methyl)carbamateYield 55%

Procedure

Following a procedure analogous to Example 27, from the carboxylic acid (6b, 390 mg, 1.41 mmol) of Example 9 or 16 and tert-butyl(2-(aminooxy)ethyl)(methyl)carbamate (436 mg) described in Reference Example 16, 347.8 mg of the title compound was afforded (yield 55%).

Sources & evidence

ORD record
ord-6cb78650e01e4e488611e3c48f9daca1
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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