(R)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acid → HCID 58760131, compound

HRID 857777Notes

Reaction equation

HRID 857777 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:17]2[CH:21]=[N:20][N:19]=[N:18]2)=[C:6]([CH:16]=1)[CH2:7][NH:8][C:9](=[O:15])[C@@H:10]1[CH2:14][CH2:13][CH2:12][NH:11]1.C(OC([NH:29][C@@H:30]([C:35](O)=[O:36])[CH2:31][CH:32]1[CH2:34][CH2:33]1)=O)(C)(C)C.Cl.CCOC(C)=O>>[CH:32]1([CH2:31][C@H:30]([C:35]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:10]2[C:9]([NH:8][CH2:7][C:6]2[CH:16]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[N:17]2[CH:21]=[N:20][N:19]=[N:18]2)=[O:15])=[O:36])[NH2:29])[CH2:34][CH2:33]1

Participants

4

Reactant 3

HCID 2756015(R)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acidHCID 21866389Hydrogen chloride-ethyl acetateHCID 69655868HCID 69655868, compound

Product 1

HCID 58760131HCID 58760131, compound

Procedure

The title compound was prepared from N-[5-fluoro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide and N-(tert-butoxycarbonyl)-3-cyclopropyl-D-alanine (Example 31, Step C) followed by deprotection with HCl-EtOAc essentially according to the procedures described in Example 31, Steps D and E. HPLC RT=0.93 min (Method B); LCMS (M+H): 402; 1H NMR (400 MHz, DMSO-d6): δ 9.86 (s, 1H), 8.66 (t, J=6 Hz, 1H), 8.22–8.35 (m, 2H), 7.64–7.67 (m, 1H), 7.38–7.39 (m, 2H), 4.18–4.30 (m, 1H), 4.00–4.22 (m, 3H), 3.73–3.82 (m, 1H), 3.52–3.58 (m, 1H), 2.0–2.13 (m, 1H), 1.77–1.94 (m, 3H), 1.65–1.74 (m, 1H), 1.52–1.61 (m, 1H), 0.77–0.85 (m, 1H), 0.44–0.48 (m, 2H), 0.05–0.17 (m, 2H).

Sources & evidence

ORD record
ord-7941b8d809594cba95067361e339273f
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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