Hydrogen chloride-ethyl acetate → HCID 23560056, compound

HRID 1058329Notes

Reaction equation

C(OC([NH:8][CH2:9][C:10]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:11]=1[CH2:12][NH:13][C:14](=[O:36])[C@@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20](=[O:35])[CH2:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O)(C)(C)C.Cl.CCOC(C)=O>CCOC(C)=O>[C:23]1([CH:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:21][C:20]([N:16]2[CH2:17][CH2:18][CH2:19][C@H:15]2[C:14]([NH:13][CH2:12][C:11]2[CH:37]=[C:38]([Cl:41])[CH:39]=[CH:40][C:10]=2[CH2:9][NH2:8])=[O:36])=[O:35])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)-1-(3,3-diphenylpropanoyl)-L-prolinamide from the previous step (0.050 g, 0.082 mmol, HPLC RT=2.9 min) was dissolved in EtOAc (2 mL) and cooled with stirring to 0° C. HCl/EtOAc (3.55M, 1.5 mL) was added. Remove bath and stir for 2 hours. HPLC analysis indicated completion and the solvent was removed under reduced pressure. The residue was triturated with Et2O and filtered to give the hydrochloride salt of the title compound as a solid. HPLC RT=1.84 min, Method B; LC-MS M+H=476, 478; 1H NMR, 400 MHz, DMSO-d6, 8.40, (t, J=6 Hz, 1H); 8.16, (br s, 2H); 7.40-7.44, (m, 4H); 7.10-7.32 (m, 9H); 4.48-4.52 (m, 1H); 4.30-4.31, (m, 2H); 4.15-4.17 (m, 1H); 4.07 (s, 2H); 3.58-3.60 (m, 1H); 3.48-3.51 (m, 1H); 2.94, (dd, J=5, 16 Hz, 1H); 1.72-1.99 (m, 5H).

Workup

temperaturecooled
customRemove bath
stirringstir for 2 hours
customthe solvent was removed under reduced pressure
customThe residue was triturated with Et2O
filtrationfiltered

Sources & evidence

ORD record: ord-38834d86d28c42e2b79dec0ef397cc5a
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515011B2

Reaction notes

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