3-Isoxazolamine → (S)-tert-Butyl 1-(2-(isoxazol-3-yl carbamoyl)-1H-pyrrol-1-ylamino)-1-oxopropan-2-ylcarbamate

HRID 525040Notes

Reaction equation

HRID 525040 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].[O:23]1[CH:27]=[CH:26][C:25]([NH2:28])=[N:24]1>>[O:23]1[CH:27]=[CH:26][C:25]([NH:28][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])=[N:24]1

Participants

3

Reactant 2

HCID 18102163-IsoxazolamineHCID 86722033(S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate

Product 1

HCID 86722059(S)-tert-Butyl 1-(2-(isoxazol-3-yl carbamoyl)-1H-pyrrol-1-ylamino)-1-oxopropan-2-ylcarbamate

Procedure

Same procedure as described in preparation 133a was used from (S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate (854 mg, 2.17 mmols) and isoxazol-3-amine (0.48 ml, 6.50 mmols). The title compound was obtained (919 mg, 55% purity, 64%).

Sources & evidence

ORD record
ord-0281437703964958a4469deec4914efb
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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