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

HRID 2363548Notes

Reaction equation

HRID 2363548 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].[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][CH2:11][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 25918977(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amineHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66590195Tert-butyl(s)-1-((3as,4r,6ar)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylamino)-1-oxopentan-2-yl(methyl)carbamate

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-L-norvaline for N-(tert-butoxycarbonyl)-L-leucine and (3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine from Step E of Example 16 for (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 221: 1H NMR (500 MHz, pyridine-d5, temperature 90° C.) δ ppm 7.36-7.38 (m, 2H), 7.28-7.31 (m, 3H), 7.21 (t, J=7.2 Hz, 1H), 4.70-4.79 (m, 1H), 4.23-4.29 (m, 1H), 3.57 (d, J=13.2 Hz, 1H), 3.47 (d, J=13.2 Hz, 1H), 2.95 (s, 3H), 2.77-2.81 (m, 1H), 2.48-2.52 (m, 1H), 2.39-2.46 (m, 2H), 2.36 (dd, J=9.0, 2.9 Hz, 1H), 2.30 (t, J=8.0 Hz, 1H), 2.07 (dq, J=12.1, 6.1 Hz, 1H), 1.92-2.03 (m, 1H), 1.72-1.86 (m, 2H), 1.50-1.59 (m, 1H), 1.47 (s, 9H), 1.36-1.44 (m, 1H), 1.25-1.35 (m, 2H), 0.86 (t, J=7.3 Hz, 3H); MS (ESI+) m/z 430 (M+H)+.

Sources & evidence

ORD record
ord-0ac689dd9f4c46209d5d49e35070a533
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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