Aniline → (S)-tert-Butyl (4-(benzyloxy)-1-((3-bromo-2-(phenylcarbamoyl)-1H-pyrrol-1-yl)amino)-1-oxobutan-2-yl)carbamate

HRID 1052392Notes

Reaction equation

HRID 1052392 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:12]([NH:14][N:15]1[CH:19]=[CH:18][C:17]([Br:20])=[C:16]1[C:21]([O:23]C)=O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C[Al](C)C>>[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:25][C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])[C:12]([NH:14][N:15]1[CH:19]=[CH:18][C:17]([Br:20])=[C:16]1[C:21](=[O:23])[NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6115AnilineHCID 16682925TrimethylaluminumHCID 86722060(S)-Methyl 1-(4-(benzyloxy)-2-(tert-butoxycarbonylamino)butanamido)-3-bromo-1H-pyrrole-2-carboxylate

Product 1

HCID 131736129(S)-tert-Butyl (4-(benzyloxy)-1-((3-bromo-2-(phenylcarbamoyl)-1H-pyrrol-1-yl)amino)-1-oxobutan-2-yl)carbamateYield 63.4%

Procedure

(S)-Methyl 1-(4-(benzyloxy)-2-((tert-butoxycarbonyl)amino)butanamido)-3-bromo-1H-pyrrole-2-carboxylate (1 g, 1.96 mmol) was treated with aniline (893 μl, 9.8 mmol) and trimethyl aluminium (2 M in toluene, 4.9 mL, 9.8 mmol) according to the method of Preparation 10a. The residue was purified using SP1® Purification System (0% to 30%, hexane-ethyl acetate) a to obtain 0.71 g (63% yield) of the title compound. Purity 100%.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 30%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-998b266345f3427eb878c65965f991ec
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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