2-(4,4-Difluorocyclohexyl)acetic acid → (R)-ethyl 3-((1-(2-(4,4-difluorocyclohexyl)acetyl)pyrrolidin-2-yl)methoxy)picolinate

HRID 2406801Notes

Reaction equation

HRID 2406801 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[NH:15]1[CH2:19][CH2:18][CH2:17][C@@H:16]1[CH2:20][O:21][C:22]1[C:23]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:24][CH:25]=[CH:26][CH:27]=1.[F:33][C:34]1([F:44])[CH2:39][CH2:38][CH:37]([CH2:40][C:41](O)=[O:42])[CH2:36][CH2:35]1.COC1C=C(OC[C@H]2CCCN2C([C@H]2CC[C@H](C(F)(F)F)CC2)=O)C(C(O)=O)=NC=1>>[F:33][C:34]1([F:44])[CH2:39][CH2:38][CH:37]([CH2:40][C:41]([N:15]2[CH2:19][CH2:18][CH2:17][C@@H:16]2[CH2:20][O:21][C:22]2[C:23]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:42])[CH2:36][CH2:35]1

Participants

4

Reactant 3

HCID 534207432-(4,4-Difluorocyclohexyl)acetic acidHCID 86762606(R)-ethyl 3-(pyrrolidin-2-ylmethoxy)picolinate bis(trifluoroacetic acid) saltHCID 178493765HCID 178493765, compound

Product 1

HCID 86666100(R)-ethyl 3-((1-(2-(4,4-difluorocyclohexyl)acetyl)pyrrolidin-2-yl)methoxy)picolinate

Procedure

The title compound was prepared according to the procedure described in Step 5 of EXAMPLE 31 using (R)-ethyl 3-(pyrrolidin-2-ylmethoxy)picolinate bis(trifluoroacetic acid) salt (EXAMPLE 34 Step 1) and 2-(4,4-difluorocyclohexyl)acetic acid instead of ammonium chloride and 5-methoxy-3-(((R)-1-(trans-4-(trifluoromethyl)cyclohexanecarbonyl)pyrrolidin-2-yl)methoxy)picolinic acid.

Sources & evidence

ORD record
ord-6c35e3c7e0dd42ae93850f78a9fa7974
Source dataset
uspto-grants-2014_08
Patent number
US08809380B2

Reaction notes

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