HCID 10842227, compound → HCID 10144654, compound

HRID 2211391Notes

Reaction equation

HRID 2211391 reaction equation
C[O:2][C:3](=[O:50])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]2[CH:29]=[C:28]([O:30]CC3C=CC=CC=3)[C:27]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[CH:26][C:25]=2[CH2:45][CH3:46])[C:12]=1[CH2:47][CH2:48][CH3:49]>C(Cl)(Cl)Cl>[CH2:47]([C:12]1[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]2[CH:29]=[C:28]([OH:30])[C:27]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[CH:26][C:25]=2[CH2:45][CH3:46])=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:50])=[O:2])[CH2:48][CH3:49]

Participants

3

Reactant 1

HCID 10842227HCID 10842227, compound

Product 1

HCID 10144654HCID 10144654, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-[2-Propyl-3-[5-[2-ethyl-4-(4-fluorophenyl)-5-(phenylmethoxy)phenoxy]pentoxy]phenoxy]benzoic acid methyl ester (3.60 g, 5.32 mmol) was submitted to de-benzylation and hydrolysis as described above for the preparation of Example 60. The product was isolated via vacuum filtration as a white crystalline solid: mp 65° C. (dec); NMR (CDCl3) 8.25 (dd, J=7.9, 1.7 Hz, 1H), 7.44 (m, 3H), 7.18 (m, 4H), 6.97 (s, 1H), 6.80 (d, J=8.2 Hz, 1H), 6.75 (d, J=8.5 Hz, 1H), 6.65 (d, J=8.1 Hz, 1H), 6.54 (s, 1H), 5.15 (bs, 1H, --OH), 4.10 (t, J=6.1 Hz, 2H), 4.05 (t, J=5.6 Hz, 2H), 2.61 (m, 4H), 1.93 (m, 4H), 1.75 (m, 2H), 1.54 (hextet, J=7.4 Hz, 2H), 1.18 (t, J=7.4 Hz, 3H), 0.89 (t, J=7.3 Hz, 3H); MS-FD m/e 572 (p); IR (CHCl3, cm-1) 3350 (b), 2965, 1739, 1605, 1496, 1455, 1238, 1108. Analysis for C35H37O6F: Calc: C, 73.41; H, 6.51; Found: C, 73.13; H, 6.59.

Workup

  1. customas described above for the preparation of Example 60
  2. customThe product was isolated via vacuum filtration as a white crystalline solid

Sources & evidence

ORD record
ord-c4a40947eda14d1fb6db67cf4bdee8d1
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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