L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → Tert-butyl(s)-1-((3as,4s,6ar)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylamino)-4-methyl-1-oxopentan-2-yl(methyl)carbamate

HRID 2363551Notes

Reaction equation

HRID 2363551 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:17]([N:24]1[CH2:28][C@H:27]2[C@@H:29]([NH2:32])[CH2:30][CH2:31][C@H:26]2[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:33](N1C[C@@H]2[C@@H](N)CC[C@@H]2C1)C1C=CC=CC=1>>[CH2:17]([N:24]1[CH2:28][C@H:27]2[C@@H:29]([NH:32][C:14](=[O:16])[C@@H:9]([N:8]([CH3:33])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH:11]([CH3:12])[CH3:13])[CH2:30][CH2:31][C@H:26]2[CH2:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 25918979(3AS,4S,6AR)-2-Benzyloctahydrocyclopenta[C]pyrrol-4-amineHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66590216Tert-butyl(s)-1-((3as,4s,6ar)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylamino)-4-methyl-1-oxopentan-2-yl(methyl)carbamate

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-L-leucine for N-(tert-butoxycarbonyl)-L-leucine and (3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine from Step C of Example 14 for (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 221: 1H NMR (501 MHz, pyridine-d5, temperature 90° C.) δ ppm 7.44-7.49 (m, 2H), 7.36-7.40 (m, 2H), 7.32-7.39 (m, 1H), 7.27 (t, J=7.4 Hz, 1H), 4.82-4.89 (m, 1H), 4.37-4.43 (m, 1H), 3.63 (d, J=13.2 Hz, 1H), 3.50 (d, J=13.0 Hz, 1H), 2.94 (s, 3H), 2.73 (dd, J=9.7, 1.8 Hz, 1H), 2.64-2.70 (m, 1H), 2.44-2.47 (m, 2H), 2.22-2.28 (m, 1H), 2.15-2.19 (m, 1H), 1.88 (ddd, J=14.1, 8.2, 6.0 Hz, 1H), 1.64-1.81 (m, 3H), 1.55-1.65 (m, 2H), 1.50 (s, 9H), 1.28-1.38 (m, 1H), 0.90-0.93 (m, 6H); MS (ESI+) m/z 444 (M+H)+.

Sources & evidence

ORD record
ord-6934fd615db8421890631bb984e2315d
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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