Sodium Hydroxide → HCID 59864753, compound

HRID 889597Notes

Reaction equation

HRID 889597 reaction equation
C([O:5][C:6](=[O:47])[CH2:7][CH2:8][N:9]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[S:10]([C:13]1[CH:18]=[CH:17][C:16]([C@H:19]([C:26](=[O:39])[NH:27][C:28]2[S:29][C:30]3[C:35]([N:36]=2)=[CH:34][CH:33]=[C:32]([O:37][CH3:38])[N:31]=3)[CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])(C)(C)C.[OH-].[Na+]>CO.O>[CH2:40]([N:9]([S:10]([C:13]1[CH:14]=[CH:15][C:16]([C@H:19]([C:26](=[O:39])[NH:27][C:28]2[S:29][C:30]3[C:35]([N:36]=2)=[CH:34][CH:33]=[C:32]([O:37][CH3:38])[N:31]=3)[CH2:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:17][CH:18]=1)(=[O:11])=[O:12])[CH2:8][CH2:7][C:6]([OH:47])=[O:5])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86625465HCID 86625465, compound

Product 1

HCID 59864753HCID 59864753, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The title I compound, 3-(benzyl-{4-[(R)-2-cyclopentyl-1-(5-methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-amino)-propionic acid tert-butyl ester (0.064 g, 0.0942 mmol) is dissolved in methanol (5 mL), to which a solution of sodium hydroxide (0.004 g, 0.0942 mmol) in water (2 mL) is added. The reaction mixture is stirred at RT overnight. The reaction mixture is then concentrated and the residue is partitioned between 1 M HCl/ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and concentrated to afford 3-(benzyl-{4-[(R)-2-cyclopentyl-1-(5-methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-amino)-propionic acid as a white foam: 1H NMR (400 MHz-CDCl3) δ 1.17 (m, 2H) 1.50 (m, 2H) 1.66 (m, 4H) 1.78 (m, 1H) 2.28 (m, 1H) 2.43 (m, 2H) 3.23 (m, 1H) 3.50 (m, 1H) 3.85 (m, 2H) 4.00 (s, 3H) 4.37 (m, 1H) 4.77 (m, 1H) 6.79 (m, 1H) 7.36 (m, 5H) 7.52 (m, 2H) 7.67 (m, 1H) 7.95 (m, 2H); LC/MS 623.3 (M+1), 621.4 (M−1). EC50 in primary enzyme assay 0.27 μM

Workup

  1. additionis added
  2. concentrationThe reaction mixture is then concentrated
  3. customthe residue is partitioned between 1 M HCl/ethyl acetate
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2dd0495b3d0b45649353ea397199566a
Source dataset
uspto-grants-2012_08
Patent number
US08252931B2

Reaction notes

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