Lithium Hydroxide → HCID 57388770, compound

HRID 2406978Notes

Reaction equation

HRID 2406978 reaction equation
[CH:1]1([CH:7]([NH:24][C:25]2[N:30]=[CH:29][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([O:38]CC)=[O:37])=[O:32])=[CH:27][CH:26]=2)[C:8]2[CH:9]=[N:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)=[N:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.[OH-].[Li+]>CO>[CH:1]1([CH:7]([NH:24][C:25]2[N:30]=[CH:29][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[O:32])=[CH:27][CH:26]=2)[C:8]2[CH:9]=[N:10][C:11]([C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=3)=[N:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67980881HCID 67980881, compound

Product 1

HCID 57388770HCID 57388770, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

In two separate reaction vessels, (+) and (−)-ethyl N-({6-[(cyclohexyl{2-[4-(trifluoromethyl)phenyl]pyrimidin-5-yl}methyl)amino]pyridin-3-yl}carbonyl)-beta-alaninate (0.050 g, 0.090 mmol) were separately dissolved in methanol (0.2 ml) and tetrahydrofuran (0.10) and treated with aqueous lithium hydroxide (0.090 ml, 0.36 mmol, 2.0M aq.). The reactions were heated to 50° C. for 12 hours. The reactions were concentrated in vacuo, then diluted with water and acidified with aqueous 1.0M hydrochloric acid. The precipitated solids were collected for both acids and dried in vacuo to give the products as single enantiomers. 1H NMR (400 MHz, CD3OD, δ): 8.91 (s, 2H), 8.60 (d, J=8.2 Hz, 2H), 8.34 (s, 1H), 8.18 (d, J=8.0 Hz, 1H), 7.80 (d, J=8.2 Hz, 2H), 7.10 (d, J=9.4 Hz, 1H), 4.79 (d, J=8.0 Hz, 2H), 3.58 (t, J=6.7 Hz, 2H), 2.60 (t, J=6.7 Hz, 2H), 1.92-2.09 (m, 2H), 1.66-1.90 (m, 3H), 1.53 (d, J=12.3 Hz, 1H), 1.05-1.43 (m, 7H). MS (M+1): 528.4.

Workup

  1. customIn two separate
  2. customreaction vessels
  3. concentrationThe reactions were concentrated in vacuo
  4. additiondiluted with water
  5. customThe precipitated solids were collected for both acids
  6. customdried in vacuo
  7. customto give the products as single enantiomers

Sources & evidence

ORD record
ord-136a4d3eab474ab3868276c6a2eab5b8
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

Loading…