Diphenylmethyl aminoxy-[3-fluoro-4,5-bis-[(2-methoxy-ethoxy)-methoxy]-phenyl]-acetate → [[[1-[3-Fluoro-4,5-bis-[(2-methoxy-ethoxy)-methoxy]-phenyl]-2-oxo-2-(diphenylmethoxy)-ethyl]-oxy]-imino]-[2-[(triphenylmethyl)-amino]-thiazol-4-yl]-acetic acid

HRID 2575Notes

Reaction equation

HRID 2575 reaction equation
[O:1]([CH:3]([C:20]1[CH:25]=[C:24]([O:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])[C:23]([O:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH3:39])=[C:22]([F:40])[CH:21]=1)[C:4]([O:6][CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])[NH2:2].O=[C:42]([C:46]1[N:47]=[C:48]([NH:51][C:52]([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[S:49][CH:50]=1)[C:43]([OH:45])=[O:44]>CO>[F:40][C:22]1[CH:21]=[C:20]([CH:3]([O:1][N:2]=[C:42]([C:46]2[N:47]=[C:48]([NH:51][C:52]([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)([C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)[S:49][CH:50]=2)[C:43]([OH:45])=[O:44])[C:4](=[O:5])[O:6][CH:7]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:25]=[C:24]([O:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])[C:23]=1[O:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH3:39]

Participants

4

Reactant 2

HCID 9829251Diphenylmethyl aminoxy-[3-fluoro-4,5-bis-[(2-methoxy-ethoxy)-methoxy]-phenyl]-acetateHCID 11133448(2-Triphenylmethylamino-4-thiazolyl)glyoxylic acid

Product 1

HCID 85053407[[[1-[3-Fluoro-4,5-bis-[(2-methoxy-ethoxy)-methoxy]-phenyl]-2-oxo-2-(diphenylmethoxy)-ethyl]-oxy]-imino]-[2-[(triphenylmethyl)-amino]-thiazol-4-yl]-acetic acidYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.640 g of the product of Step D and and 0.474 g of oxo-[2-[(triphenylmethyl)-amino]-thiazol-4-yl]-acetic acid (Belgian Patent Application No. 864,828) were stirred for 4 and a half hours under nitrogen and at ambient temperature in the presence of 20 ml of methanol. Then, the solvent was eliminated, and the residue was chromatographed on silica, eluting with a dichloromethane-methanol (95-5) mixture to obtain 0.612 g of the expected product with a Rf=0.35 [eluant: dichloromethane-methanol (9-1)].

Workup

  1. customthe residue was chromatographed on silica
  2. washeluting with a dichloromethane-methanol (95-5) mixture

Sources & evidence

ORD record
ord-0a483aea8a4b498cbaefafb7e4383a84
Source dataset
uspto-grants-1998_03
Patent number
US05728828

Reaction notes

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