Sodium Carbonate → 3-(2'-benzyloxy-biphenyl-4-yl)-(2S)-[5-chloro-2-(2-methyl-butylamino)-benzoylamino]-propionic acid

HRID 1784251Notes

Reaction equation

HRID 1784251 reaction equation
COC(=O)[C@@H](NC(=O)C1C=C(Cl)C=CC=1NCC(C)CC)CC1C=CC(Br)=CC=1.C(OC1C=CC=CC=1B(O)O)C1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].C[O:54][C:55](=[O:94])[CH:56]([NH:78][C:79](=[O:93])[C:80]1[CH:85]=[C:84]([Cl:86])[CH:83]=[CH:82][C:81]=1[NH:87][CH2:88][CH:89]([CH3:92])[CH2:90][CH3:91])[CH2:57][C:58]1[CH:63]=[CH:62][C:61]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][C:65]=2[O:70][CH2:71][C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)=[CH:60][CH:59]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:71]([O:70][C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][C:64]=1[C:61]1[CH:62]=[CH:63][C:58]([CH2:57][C@H:56]([NH:78][C:79](=[O:93])[C:80]2[CH:85]=[C:84]([Cl:86])[CH:83]=[CH:82][C:81]=2[NH:87][CH2:88][CH:89]([CH3:92])[CH2:90][CH3:91])[C:55]([OH:94])=[O:54])=[CH:59][CH:60]=1)[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 2773253(2-(Benzyloxy)phenyl)boronic acidHCID 688606913-(2'-Benzyloxy-biphenyl-4-yl)-2-[5-chloro-2-(2-methyl-butylamino)-benzoylamino]-propionic acid methyl esterHCID 688628123-(4-bromo-phenyl)-(2S)-[5-chloro-2-(2-methyl-butylamino)-benzoylamino]-propionic acid methyl ester

Product 1

HCID 575914383-(2'-benzyloxy-biphenyl-4-yl)-(2S)-[5-chloro-2-(2-methyl-butylamino)-benzoylamino]-propionic acidYield 95.3%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The methyl ester of the title compound was prepared by coupling of the 3-(4-bromo-phenyl)-(2S)-[5-chloro-2-(2-methyl-butylamino)-benzoylamino]-propionic acid methyl ester (1.24 mmol, 0.600 g) and 2-benzyloxyphenyl boronic acid (2.48 mmol, 0.567 g) with Pd (PPh3)4 (0.124 mmol, 0.143 g) as catalyst and Na2CO3 (3.732 mmol) as per Procedure D. The resulting 3-(2′-Benzyloxy-biphenyl-4-yl)-2-[5-chloro-2-(2-methyl-butylamino)-benzoylamino]-propionic acid methyl ester (0.430 g) was then hydrolyzed as per Procedure C to yield the title compound (0.400 g).

Sources & evidence

ORD record
ord-d0936e14042a432d8d096e61ad02b1e7
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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