HCID 86620601, compound → HCID 11671049, compound

HRID 1685548Notes

Reaction equation

HRID 1685548 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:42])[CH2:15][S:16][C:17]2[S:21][C:20]([NH:22][C:23](=[O:41])[C@@H:24]([C:31]3[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=3)[CH2:25][CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)(Cl)Cl.C(O)(C(F)(F)F)=O>[CH:26]1([CH2:25][C@H:24]([C:31]2[CH:32]=[CH:33][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:35][CH:36]=2)[C:23]([NH:22][C:20]2[S:21][C:17]([S:16][CH2:15][C:14](=[O:42])[N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:18][N:19]=2)=[O:41])[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 1

HCID 86620601HCID 86620601, compound

Product 1

HCID 11671049HCID 11671049, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(R)-4-(2-{2-[3-Cyclopentyl-2-(4-methanesulfonyl-phenyl)propionylamino]-thiazol-5-ylsulfanyl}-acetyl)-piperazine-1-carboxylic acid tert-butyl ester (50 mg, 78.6 mml) was dissolved in a mixture of chloroform (2 mL) and TFA (1 mL). The mixture was stirred at room temperature for 2 h and evaporated to dryness in vacuo to give white crystals of (R)-3-cyclopentyl-2-(4-methanesulfonylphenyl)-N-[5-(2-oxo-2-piperazin-1-yl-ethylsulfanyl)-thiazol-2-yl]-propionamide. 1H-NMR (CD3OD): δ 7.92 (d, 2H), 7.67 (d, 2H), 7.48 (s, 1H), 3.97 (t, 1H), 3.81 (m, 4H), 3.73 (s, 3H), 3.29-3.23 (m, 4H), 3.10 (s, 3H), 2.24-2.16 (m, 1H), 1.90-1.75 (m, 3H), 1.69-1.59 (m, 3H), 1.50 (m, 2H), 1.17 (m, 2H); HPLC-MS: m/z: 537 (M+1).

Workup

  1. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-03cc169866904366836048d51c941a93
Source dataset
uspto-grants-2012_04
Patent number
US08148412B2

Reaction notes

Loading…