Dichloromethane → HCID 67496787, compound

HRID 1628210Notes

Reaction equation

HRID 1628210 reaction equation
[O:1]=[C:2]([NH:19][C:20]1[S:24][C:23]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[N:22][CH:21]=1)[C@@H:3]([NH:11]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[NH2:11][C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:2]([NH:19][C:20]1[S:24][C:23]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[N:22][CH:21]=1)=[O:1]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 67497941HCID 67497941, compound

Product 1

HCID 67496787HCID 67496787, compoundYield 46.2%

Procedure

To a solution of (S)-tert-butyl 1-oxo-3-phenyl-1-(2-(pyridin-4-yl)thiazol-5-ylamino)propan-2-ylcarbamate (0.448 g, 1.1 mmol) in DCM (10 ml, 155 mmol) was added TFA (3.00 ml, 39 mmol). The resulting mixture was allowed to stir at rt for 3 hours. Upon completion, the mixture was concentrated and the residue was purified by HPLC to give 165 mg of (S)-2-amino-3-phenyl-N-(2-(pyridin-4-yl)thiazol-5-yl)propanamide 5.3E. 400 MHz 1H NMR (CD3OD) δ: 8.80 (d, J=8.0 Hz, 2H), 8.40 (d, J=8.0 Hz, 2H), 7.84 (s, 1H), 7.28-7.37 (m, 5H), 4.40 (dd, J=8.0, 8.0 Hz, 1H), 3.35 (obscured dd, 1H), 3.24 (dd, J=16.0, 8.0 Hz, 1H). LCMS (ES+) m/z 325.

Workup

  1. concentrationUpon completion, the mixture was concentrated
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-7fd8da21461c41dca3299f480f993fab
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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