Hydrochloric Acid → 3-isopropylprolyl-N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-L-prolinamide

HRID 857761Notes

Reaction equation

HRID 857761 reaction equation
C(OC([N:8]1[CH2:35][CH2:34][CH:33]([CH:36]([CH3:38])[CH3:37])[C@H:9]1[C:10]([N:12]1[CH2:32][CH2:31][CH2:30][C@H:13]1[C:14]([NH:16][CH2:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[N:25]1[CH:29]=[N:28][CH:27]=[N:26]1)=[O:15])=[O:11])=O)(C)(C)C.Cl>O1CCOCC1>[CH:36]([CH:33]1[CH2:34][CH2:35][NH:8][C@@H:9]1[C:10]([N:12]1[CH2:32][CH2:31][CH2:30][C@H:13]1[C:14]([NH:16][CH2:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[N:25]1[CH:29]=[N:28][CH:27]=[N:26]1)=[O:15])=[O:11])([CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 696556661-(tert-butoxycarbonyl)-3-isopropylprolyl-N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-L-prolinamide

Product 1

HCID 696561973-isopropylprolyl-N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-L-prolinamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of diastereomer A of 1-(tert-butoxycarbonyl)-3-isopropylprolyl-N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-L-prolinamide (96 mg, 0.18 mmol) in dioxane (5.0 mL) was added 4.0 N HCl in dioxane in excess. After 1 h, the solvent was removed in vacuo to give the HCl salt of the title compound as a yellow solid. LCMS (M+H): 445.3. 1H NMR (CD3OD, 400 MHz): δ 9.05 (s, 1 H), 8.38 (s, 1 H), 7.71 (s, 1 H), 7.51–7.45 (m, 2 H), 4.48–4.42 (m, 2 H), 4.39 (d, J=16.0 Hz, 1 H), 4.24 (d, J=16.4 Hz, 1 H), 3.79–3.48 (m, 3 H), 3.37–3.31 (m, 1 H), 2.44–2.39 (m, 1 H), 2.38–2.23 (m, 1 H), 2.16–2.11 (m, 1 H), 2.09–1.84 (m, 4 H), 1.79–1.71 (m, 1 H), 1.07 (d, J=6.8 Hz, 3 H), 1.01 (d, J=6.4 Hz, 3 H).

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-75ef8deb06c143699a17a75781b541af
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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