(1R)-1-(2-chlorophenyl)ethan-1-ol → 5-(4-{4-[(1R)-1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}phenyl)-4-pentenoic acid

HRID 2111025Notes

Reaction equation

HRID 2111025 reaction equation
IC1C=CC(C2C(C(O)=O)=CON=2)=CC=1.ClC1C=CC=CC=1[C@H](O)C.[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C@H:33]([O:35][C:36]([NH:38][C:39]1[C:40]([C:44]2[CH:49]=[CH:48][C:47]([CH:50]=[CH:51][CH2:52][CH2:53][C:54]([O:56]C)=[O:55])=[CH:46][CH:45]=2)=[N:41][O:42][CH:43]=1)=[O:37])[CH3:34]>>[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C@H:33]([O:35][C:36]([NH:38][C:39]1[C:40]([C:44]2[CH:45]=[CH:46][C:47]([CH:50]=[CH:51][CH2:52][CH2:53][C:54]([OH:56])=[O:55])=[CH:48][CH:49]=2)=[N:41][O:42][CH:43]=1)=[O:37])[CH3:34]

Participants

4

Reactant 3

HCID 6999092(1R)-1-(2-chlorophenyl)ethan-1-olHCID 688807933-(4-Iodophenyl)isoxazole-4-carboxylic acidHCID 68881708methyl 5-(4-{4-[(1R)-1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}phenyl)-4-pentenoate

Product 1

HCID 688817035-(4-{4-[(1R)-1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}phenyl)-4-pentenoic acid

Procedure

According to methods similar to those of Step 5 and Step 6 of Example 19 using 3-(4-iodophenyl)isoxazole-4-carboxylic acid and (R)-2-chloro-α-methylbenzyl alcohol, methyl 5-(4-{4-[(1R)-1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}phenyl)-4-pentenoate was synthesized, which was reacted in the same manner as in Example 2 to give the title compound.

Workup

  1. customwas synthesized
  2. customwhich was reacted in the same manner as in Example 2

Sources & evidence

ORD record
ord-732bdbb24332403a902fc8b37d7f467f
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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