Hydrochloric Acid → HCID 24871655, compound

HRID 1158131Notes

Reaction equation

HRID 1158131 reaction equation
[F:1][C:2]1[C:37]([CH3:38])=[CH:36][C:5]([CH2:6][C@H:7]([CH2:23][CH2:24][CH2:25][CH2:26][NH:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:8]([N:10]2[C@H](CC3C=CC=CC=3)COC2=O)=[O:9])=[CH:4][C:3]=1[CH3:39].[C-]#N.[K+].Cl.C1C[O:47]CC1.CO>>[F:1][C:2]1[C:37]([CH3:38])=[CH:36][C:5]([CH2:6][C@H:7]([CH2:23][CH2:24][CH2:25][CH2:26][NH:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:8]([NH:10][OH:47])=[O:9])=[CH:4][C:3]=1[CH3:39]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 21899815MeOH tetrahydrofuranHCID 59512587HCID 59512587, compound

Product 1

HCID 24871655HCID 24871655, compoundYield 23%

Procedure

To a solution of (R)-3-((S)-2-[4-fluoro-3,5-dimethylbenzyl)-6-(4-fluorobenzylamino)-hexanoyl]-4-benzyloxazolidin-2-one (0.030 g, 0.0561 mmol) in 2.5 mL of THF/MeOH/50% NH2OH—H2O (2:2:1), was added KCN (0.001 g, 0.015 mmol). After stirring at room temperature for overnight, the reaction mixture was acidified with concentrated HCl to pH=2 and filtered. The product was isolated by RP-HPLC eluting with 20-100% acetonitrile (0.025% TFA)/water (0.025% TFA) to give the title compound as an off-white solid (0.005 g, 23% yield). LC-MS: tR=4.8 min, m/z 391 (M+H)+, 1H NMR (300 MHz, CD3OD) δ 1.27-1.38 (m, 2H), 1.40-1.57 (m, 2H), 1.58-1.75 (m, 2H), 2.19 (s, 6H), 2.20-2.31 (m, 1H), 2.52-2.66 (m, 1H), 2.70-2.82 (m, 1H), 3.00 (t, J=7.91 Hz, 2H), 4.17 (s, 2H), 6.82 (d, J=6.74 Hz, 2H), 7.20 (t, J=8.64 Hz, 2H), 7.51 (dd, J=8.20, 5.27 Hz, 2H).

Workup

  1. filtrationfiltered
  2. customThe product was isolated by RP-HPLC
  3. washeluting with 20-100% acetonitrile (0.025% TFA)/water (0.025% TFA)

Sources & evidence

ORD record
ord-e79dd0e3f75d431782d9b8379323b494
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

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