L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → HCID 66997248, compound

HRID 2363660Notes

Reaction equation

HRID 2363660 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 25918977(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amineHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66997248HCID 66997248, compound

Procedure

tert-Butyl(R)-1-((3aS,4R,6aR)-2-Benzyloctahydrocyclopenta[c]pyrrol-4-ylamino)-4-methyl-1-oxopentan-2-yl(methyl)carbamate was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-D-leucine for N-(tert-butoxycarbonyl)-L-leucine and (3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine from Example 16 Steps A-E for (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 221: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.27 (d, J=5.9 Hz, 1H), 7.45-7.40 (m, 2H), 7.38-7.32 (m, 2H), 7.27 (dd, J=10.3, 4.3 Hz, 1H), 4.45-4.33 (m, 1H), 3.59 (d, J=13.1 Hz, 1H), 3.44 (d, J=13.2 Hz, 1H), 3.07 (d, J=23.2 Hz, 3H), 2.86-2.80 (m, 1H), 2.54-2.37 (m, 3H), 2.32 (d, J=8.6 Hz, 1H), 2.27-2.18 (m, 1H), 2.13-1.98 (m, 1H), 1.94-1.86 (m, 1H), 1.88-1.71 (m, 3H), 1.57 (td, J=13.4, 6.6 Hz, 2H), 1.48 (d, J=8.9 Hz, 9H), 1.40-1.31 (m, 1H), 0.86 (dd, J=19.8, 6.5 Hz, 6H); MS (ESI+) m/z 444 (M+H)+.

Sources & evidence

ORD record
ord-662f7ef1ccdb4a5fb92adb581e56e9e5
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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