N-carbobenzyloxyalanine → HCID 86722045, compound

HRID 525027Notes

Reaction equation

[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:17])=[O:8].[CH2:18]([O:25][C:26]([NH:28][C@@H:29]([CH3:33])[C:30](O)=[O:31])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH3:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=1[NH:9][C:7]([C:3]1[N:2]([NH:1][C:30](=[O:31])[C@@H:29]([NH:28][C:26](=[O:27])[O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:33])[CH:6]=[CH:5][CH:4]=1)=[O:8]

Participants

Reactant 2

HCID 736104N-carbobenzyloxyalanine

HCID 86722046HCID 86722046, compound

Product 1

HCID 86722045HCID 86722045, compoundYield 75%

Procedure

The title compound was prepared from 1-amino-N-(2,6-dimethylphenyl)-1H-pyrrole-2-carboxamide (324 mg, 1.41 mmol) and (S)-2-(benzyloxycarbonylamino)propanoic acid (347 g, 1.55 mmol) following the experimental procedure described in Preparation 73a. 458 mg (75% yield) of the desired compound were obtained.

Sources & evidence

ORD record: ord-73cad7163e5f4404931883c89128f052
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340547B2

Reaction notes

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