(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid → HCID 131733973, compound

HRID 710973Notes

Reaction equation

HRID 710973 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:39])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35]([NH:37][NH2:38])=[O:36])=[CH:30][CH:29]=1)([CH3:24])([CH3:23])[CH3:22]>>[C:21]([O:25][C:26](=[O:39])[NH:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35]([NH:37][NH:38][C:18]([C@@H:13]2[CH2:12][CH2:11][C@@H:10]3[CH2:17][N:14]2[C:15](=[O:16])[N:9]3[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:20])=[O:36])=[CH:30][CH:29]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 2

HCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acidHCID 122609075HCID 122609075, compound

Product 1

HCID 131733973HCID 131733973, compoundYield 74.6%

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(4-(2-hydrazinyl-2-oxoethyl)phenyl)carbamate (682.6 mg, prepared following a procedure analogous to Reference Example 5 and Reference Example 6), 550.8 mg of the title compound was afforded (yield 74.6%).

Sources & evidence

ORD record
ord-4234f8100fc543b4b684ffdf7fa10c2d
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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