1-(5-Methyl-1,2-oxazol-3-yl)methanamine → (S)-tert-Butyl 1-(2-((5-methylisoxazol-3-yl)methylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxopropan-2-ylcarbamate

HRID 525012Notes

Reaction equation

HRID 525012 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:22])[C:10]([NH:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18]([O:20]C)=O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][C:24]1[O:28][N:27]=[C:26]([CH2:29][NH2:30])[CH:25]=1>>[CH3:23][C:24]1[O:28][N:27]=[C:26]([CH2:29][NH:30][C:18]([C:14]2[N:13]([NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:22])[CH:17]=[CH:16][CH:15]=2)=[O:20])[CH:25]=1

Participants

3

Reactant 2

HCID 27763061-(5-Methyl-1,2-oxazol-3-yl)methanamineHCID 86722033(S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate

Product 1

HCID 86722032(S)-tert-Butyl 1-(2-((5-methylisoxazol-3-yl)methylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxopropan-2-ylcarbamateYield 65%

Procedure

The title compound was prepared from (S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate (750 mg, 2.41 mmol) and (5-methylisoxazol-3-yl)methanamine bromhydrate (698 mg, 3.62 mmol) following the experimental procedure described in Preparation 27a. 613 mg (63% yield) of the desired compound were obtained.

Sources & evidence

ORD record
ord-67337d821be44627a60e72d3c38f9ef2
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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