HCID 69937980, compound → HCID 44393132, compound

HRID 1058283Notes

Reaction equation

[OH:1][C@:2]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:30])[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:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:30])[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-((2S)-2-Hydroxy-2-phenyl-propanoyl)-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)-L-prolinamide from the previous step (0.125 g, 0.24 mmol) was dissolved in EtOAc (10 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, then concentrated in vacuo. The solid which had formed was triturated with Et2O and collected by filtration and washed with several portions of ether. The hydrochloride salt of the title compound was obtained as a white solid after drying overnight under high vacuum (HPLC RT=2.66 min, method A; LC-MS m/z=416.1; 1H NMR, 400 MHz, CD3OD, 7.54 ppm (s, 1H), 7.42 ppm (m, 4H), 7.34 ppm (m, 2H), 7.26 ppm (m, 1H), 4.54 ppm (d, 1H), 4.4 ppm (d, 1H), 4.3 ppm (m, 2H), 3.6 ppm (m, 1H), 3.24 ppm (m, 1H), 2.08 ppm (m, 1H), 1.8 ppm (m, 1H), 1.7 ppm (m, 1H), 1.6 ppm (s, 3H), 1.5 ppm (m, 1H)).

Workup

temperaturecooled
customInto this solution was bubbled in HCl gas for 5 min
stirringThe resulting solution was stirred at 0° C. for 30 min
concentrationconcentrated in vacuo
customThe solid which had formed
customwas triturated with Et2O
filtrationcollected by filtration
washwashed with several portions of ether

Sources & evidence

ORD record: ord-afaa8c5883a34b4da080c033a59a21d0
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515011B2

Reaction notes

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