1-((2R)-2-Cyclohexyl-2-hydroxyethanoyl)-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)-L-prolinamide → (S)-1-((R)-2-Cyclohexyl-2-hydroxy-acetyl)-pyrrolidine-2-carboxylic acid 2-aminomethyl-5-chloro-benzylamide

HRID 1058281Notes

Reaction equation

[CH:1]1([C@@H:7]([OH:35])[C:8]([N:10]2[CH2:34][CH2:33][CH2:32][C@H:11]2[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[CH2:23][NH:24]C(OC(C)(C)C)=O)=[O:13])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCOC(C)=O>[CH:1]1([C@@H:7]([OH:35])[C:8]([N:10]2[CH2:34][CH2:33][CH2:32][C@H:11]2[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[CH2:23][NH2:24])=[O:13])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

1-((2R)-2-Cyclohexyl-2-hydroxyethanoyl)-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)-L-prolinamide from the previous step (1.87 g, 3.68 mmol, HPLC RT=3.45 min) was dissolved in EtOAc (150 mL) and cooled with stirring to 0° C. HCl gas was bubbled through the solution for 10 minutes. After 2 hours at 0° C., HPLC analysis indicated complete consumption of the starting material, and the solvent was removed under reduced pressure. The resulting solid was triturated in EtOAc, filtered, and dried in vacuo to give the hydrochloride salt of the title compound as a white solid (TLC Rf=0.4 (90:10:0.5 CH2Cl2:MeOH:NH4OH); HPLC RT=2.65 min, method A; LC-MS m/z=408).

Workup

temperaturecooled
customHCl gas was bubbled through the solution for 10 minutes
customconsumption of the starting material
customthe solvent was removed under reduced pressure
customThe resulting solid was triturated in EtOAc
filtrationfiltered
customdried in vacuo

Sources & evidence

ORD record: ord-2f6982703f234544b11100ee08ac8a28
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515011B2

Reaction notes

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