HCID 86585233, compound → HCID 9835681, compound

HRID 1860536Notes

Reaction equation

HRID 1860536 reaction equation
C([O:8][NH:9][C:10](=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]1[CH2:24][CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH3:26])[CH:21]=2)[C:16]1=[O:27])C1C=CC=CC=1>CO>[OH:8][NH:9][C:10](=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]1[CH2:24][CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH3:26])[CH:21]=2)[C:16]1=[O:27]

Participants

3

Reactant 1

HCID 86585233HCID 86585233, compound

Product 1

HCID 9835681HCID 9835681, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(6-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-pentanoic acid (2b) is prepared from 6-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester (2a) (Basu, B., et al., Synth. Commun., 11, 10, 1981, 803-810) in an analogous manner to that described for 1b in example 1. 6.6 g (24.3 mmol) 1b are dissolved in 140 mL of CH2Cl2. To this solution is added sequentially 3.3 mL triethylamine, 6.9 g bis-(2-oxo-3-oxazolidinyl)-phosphorylchlorid, 3.0 g O-benzylhydroxylamine and another 10.2 mL triethylamine. After stirring over night the solution is washed with 2N HCl, then sat. NaCl sol., and evaporated. On treating with diethylether, 8.5 g 5-(6-Methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-pentanoic acid benzyloxy-amide (2c) is obtained as bright crystalls. Hydrogenation of 0.5 g of 2c in Methanol with Pd/BaCO3/Pb as a catalyst yields, after evaporation and treating with diethylether, 0.3 g of the title compound, MP 118-120° C.

Workup

  1. customafter evaporation
  2. additiontreating with diethylether, 0.3 g of the title compound, MP 118-120° C.

Sources & evidence

ORD record
ord-61d00f924d064470b43e5d7ac12dc3f6
Source dataset
uspto-grants-2003_03
Patent number
US06531472B2

Reaction notes

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