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

HRID 710993Notes

Reaction equation

HRID 710993 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])[NH:27][C@@H:28]([CH3:32])[CH2:29][O:30][NH2:31])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26](=[O:33])[NH:27][C@@H:28]([CH3:32])[CH2:29][O:30][NH:31][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])([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 2

HCID 39238211tert-Butyl (S)-(1-(aminooxy)propan-2-yl)carbamateHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid

Product 1

HCID 72549870tert-Butyl {(2S)-1-[({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]propan-2-yl}carbamateYield 87%

Procedure

Following a procedure analogous to Example 45, from the carboxylic acid (6b, 414 mg, 1.50 mmol) of Example 9 or 16 and (S)-tert-butyl(1-(aminooxy)propan-2-yl)carbamate (550 mg) described in Reference Example 19, 585.6 mg of the title compound was afforded (yield 87%).

Sources & evidence

ORD record
ord-a8d7b16291f1411da6817cb8e5cfa8e0
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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