HCID 57705674, compound → HCID 57705539, compound

HRID 1662528Notes

Reaction equation

HRID 1662528 reaction equation
[CH:1]1([C@@H:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:24]=4[F:31])=[C:19]([C@H:32](F)[C:33]([CH3:36])([CH3:35])[CH3:34])[CH:18]=3)[C:10]=2[F:38])[CH2:5][C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1.C1([C@@H](C2C=CC=C(OCC3C=CC(C4C=C(OC)C=CC=4F)=C([C@@H](F)C(C)(C)C)C=3)C=2F)C[C:44](O)=[O:45])CC1.C1([C@H](C2C=CC=C(OCC3C=CC(C4C=C(OC)C=CC=4F)=C([C@H](F)C(C)(C)C)C=3)C=2F)CC(O)=O)CC1.C1([C@H](C2C=CC=C(OCC3C=CC(C4C=C(OC)C=CC=4F)=C([C@@H](F)C(C)(C)C)C=3)C=2F)CC(O)=O)CC1>>[CH:1]1([C@H:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:24]=4[F:31])=[C:19]([C@@H:32]([O:45][CH3:44])[C:33]([CH3:34])([CH3:35])[CH3:36])[CH:18]=3)[C:10]=2[F:38])[CH2:5][C:6]([OH:8])=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 57705674HCID 57705674, compoundHCID 57706814HCID 57706814, compoundHCID 57706876HCID 57706876, compoundHCID 57707265HCID 57707265, compound

Product 1

HCID 57705539HCID 57705539, compoundYield 88%

Procedure

(3S)-3-Cyclopropyl-3-(2-fluoro-3-(((2′-fluoro-2-((1R)-1-fluoro-2,2-dimethylpropyl)-5′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)phenyl)propanoic acid or (3S)-3-cyclopropyl-3-(2-fluoro-3-(((2′-fluoro-2-((1S)-1-fluoro-2,2-dimethylpropyl)-5′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)phenyl)propanoic acid or (3R)-3-cyclopropyl-3-(2-fluoro-3-(((2′-fluoro-2-((1R)-1-fluoro-2,2-dimethylpropyl)-5′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)phenyl)propanoic acid or (3R)-3-cyclopropyl-3-(2-fluoro-3-(((2′-fluoro-2-((1S)-1-fluoro-2,2-dimethylpropyl)-5′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)phenyl)propanoic acid (83.9). The alkylation and hydrolysis were conducted in an analogous manner to Example 66.6 (using 83.B and 66.30G or 66.30H derived from peak two from the chiral separation of 66.30D from the OD-column, described herein) to yield 83.8 (0.0256 g, 88% yield). MS ESI (neg.) m/e: 525.3 (M−H)+.

Workup

  1. customThe alkylation and hydrolysis
  2. customderived from peak two from the chiral separation of 66.30D from the OD-column,

Sources & evidence

ORD record
ord-f9e07c87bbb0467abbd594d8d2fd6a98
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

Loading…