O-Benzylhydroxylamine → HCID 18623261, compound

HRID 1860541Notes

Reaction equation

HRID 1860541 reaction equation
C(OC([CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:16][CH3:17])[C:7]1=[O:18])=O)C.C([O:21][C:22](=[O:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br)C.C(OC(C1CCC2C(=CC=C(Cl)C=2)C1=O)=O)C.C(ON)C1C=CC=CC=1.COC1C=C2C(=CC=1)C(=O)C(CCCCC(O)=O)CC2.C(ONC(=O)CCCCC1CCC2C(=CC=C(OC)C=2)C1=O)C1C=CC=CC=1.C(ONC(=O)CCCCCC1CCC2C(=CC=CC=2OC)C1=O)C1C=CC=CC=1>COC1C=CC=C2C=1CCC(CCCCCC(O)=O)C2=O.C(OC(C1(CCCCCC(O)=O)CCC2C(=CC=CC=2OC)C1=O)=O)C.CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH3:17][O:16][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[CH2:14][CH2:15][CH:6]([CH:26]([CH3:27])[CH2:25][CH2:24][CH2:23][C:22]([OH:21])=[O:29])[C:7]2=[O:18]

Participants

12

Reactant 7

HCID 102313O-BenzylhydroxylamineHCID 117544Ethyl 6-bromohexanoateHCID 15643554HCID 15643554, compoundHCID 18623270HCID 18623270, compoundHCID 21218215HCID 21218215, compoundHCID 86585233HCID 86585233, compoundHCID 86758872HCID 86758872, compound

Product 1

HCID 18623261HCID 18623261, compound

Reagents, catalysts & solvents 4

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolventHCID 18623274HCID 18623274, compoundSolventHCID 70009455HCID 70009455, compoundSolvent

Procedure

5-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester (2,34 g; 8a) (Genet, J. P., et al., Tetrahedron Lett. 35 (1994) 4559-4562) is treated with ethyl-6-bromo-hexanoate in a analogues way to that described for the conversion of 3a in example 3. This resulted in a mixture of 6-(5-methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-hexanoic acid (8b) and 2-(5-Carboxy-pentyl)-5-methoxy-1-oxo-1,2,3,4-tetrahydro-naphtalene-2-carboxylic acid ethyl ester (8c) in a ratio of approximately 1:1. This mixture of acids is treated with O-benzylhydroxylamine in a similar way as described for the conversion of 2b into 2c in example 2. The crude product is subjected to column chromatography yielding an inseparable mixture of 2-(5-benzyloxycarbamoyl-pentyl)-5-methoxy-1-oxo-1,2,3,4-tetrahydro-naphtalene-2-carboxyclic acid ethyl ester (8d) and 6-(5-methoxy-1-oxo-1,2,3,4-tetrahydro-naphtalen-2-yl)-hexanoic acid benzyloxy-amide (8e). This mixture is hydrogenated in methanol with Pd/C/BaSO4 as a catalyst.

Workup

  1. additionThis mixture of acids
  2. customyielding

Sources & evidence

ORD record
ord-72696758272a468a8fc9b1ebd08abd57
Source dataset
uspto-grants-2003_03
Patent number
US06531472B2

Reaction notes

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