1-(2-hydroxy-2-phenyl-3,3,3-trifluoropropanoyl)-N-(2-tert-butyloxycarbonylaminomethyl-5-chlorobenzyl)-L-prolinamide → 1-(2-Hydroxy-2-phenyl-3,3,3-trifluoropropanoyl)-N-(2-aminomethyl-5-chlorobenzyl)-L-prolinamide

HRID 1058291Notes

Reaction equation

[OH:1][C:2]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:30]([F:33])([F:32])[F:31])[C:3]([N:5]1[CH2:29][CH2:28][CH2:27][C@H:6]1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[CH2:18][NH:19]C(OC(C)(C)C)=O)=[O:8])=[O:4]>CCOC(C)=O>[OH:1][C:2]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:30]([F:32])([F:33])[F:31])[C:3]([N:5]1[CH2:29][CH2:28][CH2:27][C@H:6]1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[CH2:18][NH2:19])=[O:8])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

1-(2-Hydroxy-2-phenyl-3,3,3-trifluoropropanoyl)-N-(2-tert-butyloxycarbonylaminomethyl-5-chlorobenzyl)-L-prolinamide from step 3 (more polar isomer, 8.5 mg, 0.015 mmol) was dissolved in EtOAc (20 mL) and cooled with stirring to 0° C. Into this solution was bubbled in HCl gas for 5 min. The resulting solution was stirred at 0° C. for 30 min. The hydrochloride salt of the title compound was obtained as a white crystalline solid after concentrating the reaction in vacuo (HPLC RT=2.78 min, method A; LC-MS m/z=470.1; 1H NMR, 400 MHz, CD3OD, 7.54 ppm (m, 3H), 7.44 ppm (d, 1H), 7.42 ppm (m, 1H), 4.5 ppm (d, 1H), 4.4 ppm (m, 2H), 4.3 ppm (m, 2H), 3.75 ppm (m, 1H), 2.7 pm (m, 1H), 2.1 ppm (m, 1H), 1.7 ppm (m, 3H)).

Workup

temperaturecooled
customInto this solution was bubbled in HCl gas for 5 min
stirringThe resulting solution was stirred at 0° C. for 30 min

Sources & evidence

ORD record: ord-7965f0f3cb404c7495d318794e5b91df
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515011B2

Reaction notes

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