Trifluoroacetic acid → HCID 66642661, compound

HRID 2108597Notes

Reaction equation

HRID 2108597 reaction equation
[CH3:1][C:2]1[C:7]([O:8][Si](C(C)(C)C)(C)C)=[C:6](Br)[C:5]([CH3:17])=[CH:4][C:3]=1O.[CH:19]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[O:30][CH2:31][O:32][CH3:33])[CH:25]=O)([CH3:21])[CH3:20].C(O)(C(F)(F)F)=O>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:25][C:24]2[CH:27]=[CH:28][C:29]([O:30][CH2:31][O:32][CH3:33])=[C:22]([CH:19]([CH3:21])[CH3:20])[CH:23]=2)[C:5]([CH3:17])=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 86052179HCID 86052179, compoundHCID 87485710HCID 87485710, compound

Product 1

HCID 66642661HCID 66642661, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 2,5-dimethyl-4-(3′-iso-propyl-4′-methoxymethoxy-benzyl)phenol was prepared from 2,5-dimethyl-4-bromo-t-butyldimethylsilyloxyphenol, and 3-iso-propyl-4-methoxymethoxy-benzaldehyde according to the procedure described in (Chiellini et al., Bioorg. Med. Chem. Lett. 10:2607 (2000)) and transformed into the title compound by the procedure used for the synthesis of compound 7-13, step b followed by example 7, step b, (0.14 g, 90%); 1H NMR (300 MHz, CD3OD): δ 6.88 (d, J=8.7 Hz, 2H), 6.79 (s, 1H), 6.64-6.72 (m, 2H), 4.20 (d, J=10.2 Hz, 2H), 3.80 (s, 2H), 3.10-3.15 (m, 1H), 2.22 (s, 3H), 2.20 (s, 3H), 1.17 (d, J=6.9 Hz, 6H); LC-MS m/z=365 [C20H25O6P+H]+; HPLC conditions: ODSAQ AQ-303-5 column; mobile phase=CH3OH: 0.05% TFA (7:3) flow rate=1.0 mL/min; detection=LUV @ 254 nm retention time in min: 10.96; Anal Calcd for (C20H25O6P+0.3H2O): C, 61.84; H, 6.92. Found: C, 61.60; H, 6.72.

Sources & evidence

ORD record
ord-9477cc26217e422bb6a565a7593226c8
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

Loading…