HCID 69939144, compound → HCID 59038226, compound

HRID 1058269Notes

Reaction equation

[OH:1][C@H:2]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[C:3]([N:5]1[CH2:30][CH2:29][CH2:28][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[CH:18]([NH:20]C(OC(C)(C)C)=O)[CH3:19])=[O:8])=[O:4]>CCOC(C)=O>[OH:1][C@H:2]([CH:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1)[C:3]([N:5]1[CH2:30][CH2:29][CH2:28][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[CH:18]([NH2:20])[CH3:19])=[O:8])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

1-((2R)-2-Hydroxy-2-cyclohexylethanoyl)-N-(2-(1-(tert-butyloxycarbonylamino)ethyl)-5-chlorobenzyl)-L-prolinamide from the previous step (0.40 g, 0.077 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 of the title compound was obtained as a white solid after drying under high vacuum (HPLC RT=2.72 min, method A; LC-MS m/z=422.1; 1H NMR, 400 MHz, CD3OD, 7.65 ppm (d, 1H), 7.35 ppm (s, 1H), 7.25 ppm (d, 1H), 4.81 ppm (dd, 2H), 4.24 ppm (q, 1H), 4.1 ppm (m, 2H), 3.74 ppm (m, 1H), 3.64 ppm (m, 1H), 2.2 ppm (m, 2H), 2.08 ppm (m, 2H), 1.94 ppm (m, 4H), 1.16 ppm (d, 3H), 1.2 ppm (m, 7H)).

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-179fc268bdca447aa21dfac6d0bfbcf6
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515011B2

Reaction notes

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