Phenylacetylene → [4-(3-Cyclopentylmethoxy-5-phenylethynyl-phenylsulfanyl)-2-methyl-phenoxy]-acetic Acid Ethyl Ester

HRID 1969256Notes

Reaction equation

HRID 1969256 reaction equation
C(OC(=O)COC1C=CC(SC2C=C(OC3CCCC3)C=C(Br)C=2)=CC=1C)C.C1(C#C)C=CC=CC=1.[CH2:37]([O:39][C:40](=[O:77])[CH2:41][O:42][C:43]1[CH:48]=[CH:47][C:46]([S:49][C:50]2[CH:55]=[C:54]([C:56]#[C:57][C:58]3[CH:63]=[CH:62][C:61](CO)=[CH:60][CH:59]=3)[CH:53]=[C:52]([O:66][CH2:67][CH2:68][C:69]3C=C[C:72](Cl)=[CH:71][CH:70]=3)[CH:51]=2)=[CH:45][C:44]=1[CH3:76])[CH3:38]>>[CH2:37]([O:39][C:40](=[O:77])[CH2:41][O:42][C:43]1[CH:48]=[CH:47][C:46]([S:49][C:50]2[CH:55]=[C:54]([C:56]#[C:57][C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)[CH:53]=[C:52]([O:66][CH2:67][CH:68]3[CH2:72][CH2:71][CH2:70][CH2:69]3)[CH:51]=2)=[CH:45][C:44]=1[CH3:76])[CH3:38]

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 57791928[4-(3-Bromo-5-cyclopentyloxy-phenylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl esterHCID 67024299{4-[3-[2-(4-Chloro-phenyl)-ethoxy]-5-(4-hydroxymethyl-phenylethynyl)-phenylsulfanyl]-2-methylphenoxy}-acetic acid ethyl ester

Product 1

HCID 67171305[4-(3-Cyclopentylmethoxy-5-phenylethynyl-phenylsulfanyl)-2-methyl-phenoxy]-acetic Acid Ethyl Ester

Procedure

The title product was prepared from [4-(3-Bromo-5-cyclopentyloxy-phenylsulfanyl)-2-methyl-phenoxy]-acetic acid ethyl ester (300 mg; 0.63 mmol), phenylacetylen (191.7 mg; 1.88 mmol) applying the procedure described for {4-[3-[2-(4-Chloro-phenyl)-ethoxy]-5-(4-hydroxymethyl-phenylethynyl)-phenylsulfanyl]-2-methyl-phenoxy}-acetic acid ethyl ester. The crude product was purified by preparative HPLC (method B). Yield: 200 mg (64%). HPLC-MS: m/z: 500.8 (M)+; Rt: 3.30 min.

Workup

  1. customThe crude product was purified by preparative HPLC (method B)

Sources & evidence

ORD record
ord-deb6437a8da94c8da29c27190157aa8a
Source dataset
uspto-grants-2013_04
Patent number
US08426473B2

Reaction notes

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