Trifluoroacetic acid → HCID 131737031, compound

HRID 58913Notes

Reaction equation

HRID 58913 reaction equation
[CH3:1][C@@:2]1([C:5](=[O:38])[C@@H:6]([NH:14][C:15](=[O:37])[C@@H:16]([NH:24][C:25](=[O:36])[C@@H:26]([NH:28]C(=O)OC(C)(C)C)[CH3:27])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][O:3]1.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C(Cl)Cl>[OH:45][C:39]([C:41]([F:44])([F:43])[F:42])=[O:40].[NH2:28][C@@H:26]([CH3:27])[C:25]([NH:24][C@@H:16]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C:15]([NH:14][C@@H:6]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([C@:2]1([CH3:1])[CH2:4][O:3]1)=[O:38])=[O:37])=[O:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131737032tert-butyl ((S)-1-(((S)-1-(((S)-1-((S)-2-methyloxiran-2-yl)-1-oxo-3-phenylpropan-2-yl)amino)-1-oxo-3-(pyridin-2-yl)propan-2-yl)amino)-1-oxopropan-2-yl)carbamate

Product 1

HCID 131737031HCID 131737031, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl ((S)-1-(((S)-1-(((S)-1-((S)-2-methyloxiran-2-yl)-1-oxo-3-phenylpropan-2-yl)amino)-1-oxo-3-(pyridin-2-yl)propan-2-yl)amino)-1-oxopropan-2-yl)carbamate (315 mg, 0.600 mmol) was added DCM (4 mL) followed by TFA (2 mL). The reaction mixture was allowed to stand for 2 h at which time it was concentrated to provide (S)-2-((S)-2-aminopropanamido)-N-((S)-1-((S)-2-methyloxiran-2-yl)-1-oxo-3-phenylpropan-2-yl)-3-(pyridin-2-yl)propanamide TFA salt as a yellow oil that was carried forward without further purification. MS (EI) for C25H28F3N4O5, found 425.3 [M-TFA]+.

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-486e65784b044a7c803518f991ec6fe5
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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