Hydrogen chloride-ethyl acetate → HCID 58760175, compound

HRID 857752Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

N-(tert-butoxycarbonyl)-3-cyclopropyl-D-alanyl-N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-L-prolinamide from the previous step (0.058 g, 0.112 mmol) was dissolved in EtOAc (2 mL) and cooled with stirring to 0° C. HCl/EtOAc (3.55M, 1.5 mL) was added. The bath was removed and the mixture stirred for 2 hours. HPLC analysis indicated completion and the solvent was removed under reduced pressure. The residue was triturated with EtOAc and filtered to give the hydrochloride salt of 3-cyclopropyl-D-alanyl-N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-L-prolinamide as a solid. (0.045 g). HPLC RT=1.04 min, Method B; LCMS (M+H): 417, 419; 1H NMR (400 MHz, DMSO-d6): δ 8.96, (s, 1H), 8.67 (t, J=6 Hz, 1H), 8.27–8.33 (m, 3H), 7.50–7.56 (m, 3H), 4.32 (dd, J=2, 9 Hz, 1H), 4.10–4.25 (m, 2H), 3.78–3.86 (m, 1H), 3.54–3.60 (m, 1H), 2.06–2.11 (m, 1H), 1.81–1.93 (m, 3H), 1.68–1.75 (m, 1H, 154–1.60 (m, 1H), 0.77–0.85 (m, 1H), 0.44–0.48 (m, 2H), 0.07–0.16 (m, 2H).

Workup

temperaturecooled
customThe bath was removed
stirringthe mixture stirred for 2 hours
customthe solvent was removed under reduced pressure
customThe residue was triturated with EtOAc
filtrationfiltered

Sources & evidence

ORD record: ord-f558854c0835478cb3e12b4c15362872
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144899B2

Reaction notes

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