Trifluoroacetic acid → (S)-2-amino-3-cyano-N-((S)-1-(((S)-3-(cyclopent-1-en-1-yl)-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl)amino)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)propanamide

HRID 58801Notes

Reaction equation

HRID 58801 reaction equation
[C:1]([CH2:3][C@H:4]([NH:34]C(=O)OC(C)(C)C)[C:5]([NH:7][C@@H:8]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C:9]([NH:11][C@@H:12]([CH2:19][C:20]1[CH2:24][CH2:23][CH2:22][CH:21]=1)[C:13]([C@@:15]1([CH3:18])[CH2:17][O:16]1)=[O:14])=[O:10])=[O:6])#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:34][C@@H:4]([CH2:3][C:1]#[N:2])[C:5]([NH:7][C@@H:8]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C:9]([NH:11][C@@H:12]([CH2:19][C:20]1[CH2:24][CH2:23][CH2:22][CH:21]=1)[C:13]([C@@:15]1([CH3:18])[CH2:17][O:16]1)=[O:14])=[O:10])=[O:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117607799tert-butyl ((S)-3-cyano-1-(((S)-1-(((S)-3-(cyclopent-1-en-1-yl)-1-((R)-2-methyl oxiran-2-yl)-1-oxopropan-2-yl)amino)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)carbamate

Product 1

HCID 117690423(S)-2-amino-3-cyano-N-((S)-1-(((S)-3-(cyclopent-1-en-1-yl)-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl)amino)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)propanamideYield 138.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl ((S)-3-cyano-1-(((S)-1-(((S)-3-(cyclopent-1-en-1-yl)-1-((R)-2-methyl oxiran-2-yl)-1-oxopropan-2-yl)amino)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)carbamate (0.59 g, 1.0 mmol) in DCM (10 mL) was added TFA (5 mL). The reaction mixture was stirred for 15 min at ambient temperature then concentrated to dryness to afford (S)-2-amino-3-cyano-N-((S)-1-(((S)-3-(cyclopent-1-en-1-yl)-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl)amino)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)propanamide (650 mg, quant.) as its TFA salt, which was used directly without further purification.

Workup

  1. concentrationthen concentrated to dryness

Sources & evidence

ORD record
ord-beded230f9154ec99dbd22174a71ec1f
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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