2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol → (+/-)-10-(3-Hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-6-(hydroxymethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575282Notes

Reaction equation

HRID 575282 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH:10]([CH2:12][OH:13])[CH2:9][N:8]3[CH:14]=[C:15]([C:17]([NH2:19])=[O:18])[N:16]=[C:7]3[C:6]=2[CH:20]=1.[CH3:21][C:22]1[O:26][N:25]=[C:24]([C:27]([OH:31])([C:29]#[CH:30])[CH3:28])[CH:23]=1>>[OH:31][C:27]([C:24]1[CH:23]=[C:22]([CH3:21])[O:26][N:25]=1)([CH3:28])[C:29]#[C:30][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH:10]([CH2:12][OH:13])[CH2:9][N:8]3[CH:14]=[C:15]([C:17]([NH2:19])=[O:18])[N:16]=[C:7]3[C:6]=2[CH:20]=1

Participants

3

Reactant 2

HCID 582217592-(5-Methylisoxazol-3-yl)but-3-yn-2-olHCID 8669331210-Bromo-6-(hydroxymethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 89754691(+/-)-10-(3-Hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-6-(hydroxymethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 40%

Procedure

Similar to as described in General Procedure G, racemic 10-bromo-6-(hydroxymethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was reacted with racemic 2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol to give the titled compound as a yellow solid (mixture of diasteromers, 98 mg, 40%).

Sources & evidence

ORD record
ord-5fd439d8c7c041c781583d4c1ece4941
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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