Benzyl 4-carboxyphenylacetate → Pivalic acid (R)-6-{2-[(4-carboxymethylbenzoyl)ethoxycarbonylmethylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

HRID 2424225Notes

Reaction equation

HRID 2424225 reaction equation
C(OC(CNC1C=C(OC)C=CC=1[C@@H]1CCC2C=C(OC(=O)C(C)(C)C)C=CC=2C1)=O)C.C(OC(CC1C=CC(C(O)=O)=CC=1)=O)C1C=CC=CC=1.C([O:60][C:61]([CH2:63][C:64]1[CH:103]=[CH:102][C:67]([C:68]([CH2:70][CH2:71][O:72][C:73]([CH2:75][NH:76][C:77]2[CH:82]=[C:81]([O:83][CH3:84])[CH:80]=[CH:79][C:78]=2[C@@H:85]2[CH2:94][CH2:93][C:92]3[CH:91]=[C:90]([O:95][C:96](=[O:101])[C:97]([CH3:100])([CH3:99])[CH3:98])[CH:89]=[CH:88][C:87]=3[CH2:86]2)=[O:74])=[O:69])=[CH:66][CH:65]=1)=[O:62])C1C=CC=CC=1>CO.[Pd]>[C:61]([CH2:63][C:64]1[CH:65]=[CH:66][C:67]([C:68]([CH2:70][CH2:71][O:72][C:73]([CH2:75][NH:76][C:77]2[CH:82]=[C:81]([O:83][CH3:84])[CH:80]=[CH:79][C:78]=2[C@@H:85]2[CH2:94][CH2:93][C:92]3[CH:91]=[C:90]([O:95][C:96](=[O:101])[C:97]([CH3:98])([CH3:100])[CH3:99])[CH:89]=[CH:88][C:87]=3[CH2:86]2)=[O:74])=[O:69])=[CH:102][CH:103]=1)([OH:62])=[O:60]

Participants

6

Reactant 3

HCID 19966080Benzyl 4-carboxyphenylacetateHCID 57934485HCID 57934485, compoundHCID 86605269pivalic acid (R)-6-{2-[(4-benzyloxycarbonylmethylbenzoyl)ethoxycarbonylmethylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 86605268Pivalic acid (R)-6-{2-[(4-carboxymethylbenzoyl)ethoxycarbonylmethylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl esterYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

From pivalic acid (R)-6-[2-(ethoxycarbonylmethylamino)-4-methoxyphenyl]-5,6,7,8-tetrahydronaphthalen-2-yl ester (150 mg) and 4-benzyloxycarbonylmethylbenzoic acid (138 mg), according to an analogous synthetic method to Preparation Example 154, obtained was pivalic acid (R)-6-{2-[(4-benzyloxycarbonylmethylbenzoyl)ethoxycarbonylmethylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (200 mg). A solution thereof in methanol (5 ml) was subjected to a catalytic reduction in the presence of 10% palladium-activated charcoal (40 mg) for 2 hours at room temperature under hydrogen atmosphere at ambient pressure. After filtration through celite pad, the solution was concentrated in vacuo to provide the title compound (170 mg).

Workup

  1. customobtained
  2. filtrationAfter filtration through celite pad
  3. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-62e2c23c6f5f4cf49ac66c19aedead24
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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