HCID 68604109, compound → HCID 68606976, compound

HRID 2267664Notes

Reaction equation

HRID 2267664 reaction equation
FC1C=C(CC(N[C@H](C(O)=O)C(C)C)=O)C=C(F)C=1.[F:20][C:21]1[CH:22]=[C:23]([CH2:28][C:29]([NH:31][C@H:32]([C:37]([O:39]C)=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:30])[CH:24]=[C:25]([F:27])[CH:26]=1>>[F:20][C:21]1[CH:22]=[C:23]([CH2:28][C:29]([NH:31][C@H:32]([C:37]([OH:39])=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:30])[CH:24]=[C:25]([F:27])[CH:26]=1

Participants

3

Reactant 2

HCID 68604109HCID 68604109, compoundHCID 68604940HCID 68604940, compound

Product 1

HCID 68606976HCID 68606976, compoundYield 80.9%

Procedure

A method similar to that used for the preparation of (107b) was used except that methyl N-[(3,5-difluorophenyl)acetyl]-L-leucinate (108a) (280 mg) was used instead of methyl N-[(3,5-difluorophenyl)acetyl]-L-valinate to afford the desired product (216 mg). 1H NMR (300 MHz, CDCl3) δ 0.83 (d, 3, J=6 Hz), 0.89 (d, 3H, J=6 Hz), 1.51 (m, 3H), 3.52 (s, 2H), 4.22 (m, 1H), 7.07 (m, 3H), 8.41 (d, 1H, J=8 Hz), 12.54 (s, 1H).

Sources & evidence

ORD record
ord-6b98fcabbff64ad0ab9b677292b2c718
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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