L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → HCID 66590974, compound

HRID 2363609Notes

Reaction equation

HRID 2363609 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].[F:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:27]2[CH2:31][C@@H:30]3[C@@H:32]([NH2:35])[CH2:33][CH2:34][C@@H:29]3[CH2:28]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1.[CH2:36](N1C[C@@H]2[C@@H](N)CC[C@@H]2C1)C1C=CC=CC=1>>[F:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([N:27]2[CH2:31][C@@H:30]3[C@@H:32]([NH:35][C:14](=[O:16])[C@@H:9]([N:8]([CH3:36])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH:11]([CH3:12])[CH3:13])[CH2:33][CH2:34][C@@H:29]3[CH2:28]2)(=[O:25])=[O:26])=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 66590552HCID 66590552, compoundHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66590974HCID 66590974, compound

Procedure

tert-Butyl(S)-1-((3aR,4S,6aS)-2-(4-fluorophenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)-4-methyl-1-oxopentan-2-yl(methyl)carbamate was prepared by substituting (S)-2-(tert-butoxycarbonyl(methyl)amino)-4-methylpentanoic acid for N-(tert-butoxycarbonyl)-L-leucine and (3aR,4S,6aS)-2-(4-fluorophenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine from Example 261 Step A for (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 221: 1H NMR (400 MHz, pyridine-d5) δ ppm 7.94 (dd, J=8.1, 5.2, 2H), 7.44-7.37 (m, 1H), 7.20 (t, J=8.5, 2H), 4.85-4.77 (m, 1H), 4.12-4.03 (m, 1H), 3.61-3.55 (m, 1H), 3.27-3.21 (m, 1H), 3.13-3.02 (m, 2H), 2.93 (s, 3H), 2.59-2.44 (m, 2H), 1.83 (ddd, J=37.1, 15.2, 5.0, 4H), 1.50 (d, J=0.6, 2H), 1.46 (d, J=0.8, 9H), 1.33-1.22 (m, 1H), 0.89 (t, J=7.2, 6H); MS (ESI+) m/z 512 (M+H)+.

Sources & evidence

ORD record
ord-b2705b7609f544abae4f4833ee6d65d4
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

Loading…