O-Benzylhydroxylamine → HCID 18623270, compound

HRID 1860535Notes

Reaction equation

HRID 1860535 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=2)[C:7]1=[O:18])=O)C.[O:19]=[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][CH:21]1[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[CH2:52]([O:59][NH2:60])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:17][O:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:18])[CH:6]([CH2:4][CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])[CH2:15][CH2:14]2.[CH2:52]([O:59][NH:60][C:34](=[O:36])[CH2:33][CH2:32][CH2:31][CH2:30][CH:21]1[CH2:22][CH2:23][C:24]2[C:29](=[CH:28][CH:27]=[C:26]([O:3][CH3:1])[CH:25]=2)[C:20]1=[O:19])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

8

Reactant 4

HCID 102313O-BenzylhydroxylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 110757986-Methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid ethyl esterHCID 18623289HCID 18623289, compound2×

Product 2

HCID 18623270HCID 18623270, compoundHCID 86585233HCID 86585233, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

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. washis washed with 2N HCl
  2. customsat. NaCl sol., and evaporated
  3. additionOn treating with diethylether

Sources & evidence

ORD record
ord-b91b459249634240b631afedc5c2b336
Source dataset
uspto-grants-2003_03
Patent number
US06531472B2

Reaction notes

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