Hydrogen chloride-ethyl acetate → 3-Cyclopropyl-D-alanyl-N-[5-fluoro-2-{1H-1,2,4-triazol-1-yl}benzyl]-L-prolinamide

HRID 857775Notes

Reaction equation

HRID 857775 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]([F: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]([F: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

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 69656183N-{tert-butoxycarbonyl}-3-cyclopropyl-D-alanyl-N-[5-fluoro-2-{1H-1,2,4-triazol-1-yl}benzyl]-L-prolinamide

Product 1

HCID 587601413-Cyclopropyl-D-alanyl-N-[5-fluoro-2-{1H-1,2,4-triazol-1-yl}benzyl]-L-prolinamideYield 79.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-{tert-butoxycarbonyl}-3-cyclopropyl-D-alanyl-N-[5-fluoro-2-{1H-1,2,4-triazol-1-yl }benzyl]-L-prolinamide (35 mg, 0.069 mmol) in EtOAc (1 mL) was treated with 1 mL of 3.5N HCl/EtOAc at 0° C. for 1 h and at room temperature for 3 h. The solvent was removed under reduced pressure and the residue triturated with EtOAc to give 22 mg of the title compound as the hydrochloride salt. 1H NMR (400 MHz, CDCl3): d 8.9 (s, 1H), 8.73 (br s, 1H), 8.35 (br, 2H), 8.23 (s, 1H), 7.48–7.51 (m, 1H), 7.24–7.29 (m, 2H), 4.27–4.30 (d, J=8.52 Hz, 1H), 4.07–4.14 (m, 3H), 3.55 (m, 2H), 2.09 (m, 1H), 1.84–1.88 (m, 3H), 1.67–1.72 (m, 1H), 1.51–1.55 (m, 1H), 0.78 (m, 1H), 0.42 (m, 2H), 0.06–0.11 (m, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue triturated with EtOAc

Sources & evidence

ORD record
ord-fd6fee739b834280b977bce41f1a84a4
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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