Sodium hydride → HCID 86751021, compound

HRID 263816Notes

Reaction equation

HRID 263816 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@:9]1([C:20]([O:22][CH3:23])=[O:21])[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([OH:19])[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[C:27]1[CH:38]=[CH:37][CH:36]=[CH:35][C:28]=1[C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30].C(OCC)(=O)C.CCCCCC>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@:9]1([C:20]([O:22][CH3:23])=[O:21])[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([O:19][C:27]3[CH:38]=[CH:37][CH:36]=[CH:35][C:28]=3[C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 13788730HCID 13788730, compoundHCID 21226206Ethyl acetate hexaneHCID 86751022HCID 86751022, compound

Product 1

HCID 86751021HCID 86751021, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In analogy to Example 4.1.a, 2.5 g (7.78 mmol) of methyl (S)-2-(tert.butoxycarbonylamino)-8-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate in 5 ml of pyridine were reacted at 130° for 2 hours with 370 mg of sodium hydride dispersion, 2.23 g (10.9 mmol) of copper bromide-dimethyl sulphide complex and 4.48 g (15.56 mmol) of prop-2-enyl 2-iodobenzoate. After chromatography on 500 g of silica gel with ethyl acetate/hexane (1:9→1:1) there were obtained 2.98 g (80%) of methyl (S)-2-(tert.butoxycarbonylamino)-8-[2-(prop-2-enyloxycarbonyl)phenoxy]-1,2,3,4-tetrahydronaphthalene-2-carboxylate as a viscous oil. [α]D ==57.0° (c=0.4, chloroform

Sources & evidence

ORD record
ord-b002059380844a98b3337f8c03c7f2de
Source dataset
uspto-grants-1997_07
Patent number
US05644024

Reaction notes

Loading…