{(S)-1-[(2S,4R)-4-(3-Methyl-but-2-enyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester → [(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxy-7-methyl-oct-6-enyl]carbamic acid tert-butyl ester

HRID 1373097Notes

Reaction equation

HRID 1373097 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C@@H:16]1[CH2:20][C@@H:19]([CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[C:18](=[O:26])[O:17]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH:28]12[CH2:34][CH:31]([CH2:32][CH2:33]1)[CH2:30][CH:29]2[NH:35]C(=O)[C@H](C)C[C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC1C=CC=CC=1>>[C:1]([O:5][C:6](=[O:27])[NH:7][C@@H:8]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C@@H:16]([OH:17])[CH2:20][C@H:19]([C:18](=[O:26])[NH:35][CH:29]1[CH2:30][CH:31]2[CH2:34][CH:28]1[CH2:33][CH2:32]2)[CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 12015737{(S)-1-[(2S,4R)-4-(3-Methyl-but-2-enyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl esterHCID 86596503(2R,4S,5S)-5-t-Butoxycarbonylamino-4-hydroxy-2-methyl-6-phenylhexanoic acid (bicyclo[2.2.1]hept-2-yl)amide

Product 1

HCID 69507684[(1S,2S,4R)-1-Benzyl-4-(bicyclo[2.2.1]hept-2-ylcarbamoyl)-2-hydroxy-7-methyl-oct-6-enyl]carbamic acid tert-butyl esterYield 60%

Procedure

{(S)-1-[(2S,4R)-4-(3-Methyl-but-2-enyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (D5) was treated with (±)exo-norbornylamine as described in D3 to afford D6 as a white solid (60%).

Sources & evidence

ORD record
ord-b2ed7cc5fe3641929660154b8213a09f
Source dataset
uspto-grants-2007_01
Patent number
US07160905B2

Reaction notes

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