HCID 57825087, compound → HCID 67346927, compound

HRID 1668757Notes

Reaction equation

HRID 1668757 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH3:23])[CH:16]=3)[CH2:13][O:12][C:11]([NH2:14])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C@@:9]2([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH3:23])[CH:16]=3)[CH2:13][O:12][C:11]([NH2:14])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 1

HCID 57825087HCID 57825087, compound

Product 1

HCID 67346927HCID 67346927, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.90 g of (RS)-4-(3-bromo-4-fluoro-phenyl)-4-(4-methoxy-3-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamine (Building Block E) in dichloromethane was divided in 200 mg aliquots which were separated on chiral HPLC (Chiralpak AD) using a 90:10-mixture of heptane and ethanol as the eluent. The fractions of the first eluting enantiomer were combined to give 406 mg of the (S)-(+)-4-(3-bromo-4-fluoro-phenyl)-4-(4-methoxy-3-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamine as a white solid. The later eluting enantiomer (R)-4-(3-bromo-4-fluoro-phenyl)-4-(4-methoxy-3-methyl-phenyl)-4,5-dihydro-oxazol-2-ylamine was isolated to give 381 mg as a white solid.

Workup

  1. customwere separated on chiral HPLC (Chiralpak AD)

Sources & evidence

ORD record
ord-9b8b828534ff4309b07da7d7db88b833
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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