HCID 18318362, compound → HCID 54070080, compound

HRID 849870Notes

Reaction equation

[C:1]([O:5][C:6](=[O:30])[NH:7][C@@H:8](CS(C1C=CC=CC=1)(=O)=O)[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[Si:31]([O:38][CH2:39][CH:40]([CH2:43][C:44]1[CH:53]=[CH:52][C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=1)C=O)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].[CH2:54](OCC)[CH3:55].CCCCCCC>>[C:1]([O:5][C:6](=[O:30])[NH:7][C@H:8]([CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[CH:54]=[CH:55][CH:40]([CH2:39][O:38][Si:31]([C:34]([CH3:36])([CH3:35])[CH3:37])([CH3:33])[CH3:32])[CH2:43][C:44]1[CH:45]=[CH:46][C:47]2[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:53]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

Reactant 3

HCID 18318362HCID 18318362, compound

HCID 21897273Diethylether heptane

HCID 54424850HCID 54424850, compound

Product 1

HCID 54070080HCID 54070080, compound

Procedure

This compound was prepared as in example 9. ((1R)-1-benzenesulfonylmethyl-2-(2-naphthyl)ethyl)carbamic acid tert-butylester (3.71 g; 8.74 mmol) and 2-(tert-butyldimethylsilanyloxymethyl)-3-(2-naphthyl)propionaldehyde (4.3 g; 13.11 mmol) were used as starting materials. Chromatography was carried out using diethylether/heptane 1:3 as eluent on silica (5×25 cm) to afford 2.20 g of ((1R)-4-(tert-butyldimethylsilanyloxymethyl)-1-((2-naphthyl)methyl)-5-(2-naphthyl)pent-2-enyl)carbamic acid tert-butyl ester as a mixture of isomers.

Workup

customThis compound was prepared as in example 9

Sources & evidence

ORD record: ord-0e74fb4d19954797b87e9c8e2f427313
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06013658

Reaction notes

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