L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → HCID 66591128, compound

HRID 2363572Notes

Reaction equation

HRID 2363572 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])C)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]([F:38])([F:37])[C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:28]2[CH2:32][C@@H:31]3[C@@H:33]([NH2:36])[CH2:34][CH2:35][C@@H:30]3[CH2:29]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1.[CH2:39](N1C[C@@H]2[C@@H](N)CC[C@@H]2C1)C1C=CC=CC=1>>[CH3:39][N:8]([C@@H:9]([CH2:10][CH2:11][CH3:13])[C:14](=[O:16])[NH:36][C@@H:33]1[C@@H:31]2[C@@H:30]([CH2:29][N:28]([S:25]([C:22]3[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:37])[F:38])=[CH:24][CH:23]=3)(=[O:26])=[O:27])[CH2:32]2)[CH2:35][CH2:34]1)[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 66590926HCID 66590926, compoundHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66591128HCID 66591128, compound

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-L-norvaline for N-(tert-butoxycarbonyl)-L-leucine and (3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine from Step A of Example 256 for (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 221: 1H NMR (400 MHz, pyridine-d5, temperature 90° C.) δ ppm 8.06-8.09 (m, 2H), 7.79-7.82 (m, 2H), 7.40 (d, J=3.1 Hz, 1H), 4.66-4.76 (m, 1H), 4.07 (p, J=6.8 Hz, 1H), 3.65 (dd, J=10.2, 3.4 Hz, 1H), 3.28 (dd, J=10.2, 7.7 Hz, 1H), 3.06-3.17 (m, 2H), 2.93 (s, 3H), 2.53-2.62 (m, 1H), 2.45-2.53 (m, 1H), 1.93-2.02 (m, 1H), 1.86-1.95 (m, 1H), 1.70-1.85 (m, 2H), 1.47-1.57 (m, 1H), 1.45 (s, 9H), 1.27-1.37 (m, 2H), 1.22-1.32 (m, 1H), 0.86 (t, J=7.4 Hz, 3H); MS (ESI+) m/z 548 (M+H)+.

Sources & evidence

ORD record
ord-9a7a66f9bcb345ceb16e93227c08379e
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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