Sodium Hydroxide → HCID 21092424, compound

HRID 1348939Notes

Reaction equation

HRID 1348939 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][CH:6]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]([C:18](=[O:38])[CH2:19][C:20]1[CH:36]=[C:35]([CH3:37])[C:23]3[N:24]=[C:25]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH3:34])[O:26][C:22]=3[CH:21]=1)[NH:13][CH2:12][CH2:11]2)[CH3:7])C.[OH-].[Na+]>C(O)C>[CH3:37][C:35]1[C:23]2[N:24]=[C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[O:26][C:22]=2[CH:21]=[C:20]([CH2:19][C:18]([CH:14]2[C:15]3[C:10](=[CH:9][C:8]([CH:6]([CH3:7])[CH2:5][C:4]([OH:39])=[O:3])=[CH:17][CH:16]=3)[CH2:11][CH2:12][NH:13]2)=[O:38])[CH:36]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69143347HCID 69143347, compound

Product 1

HCID 21092424HCID 21092424, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 3-{((4-methyl-2-o-tolylamino-benzoxazol-6-yl)-acetyl)-1,2,3,4-tetrahydro-isoquinolin -6-yl}-butanoic acid ethyl ester [0.1 g, Reference Example 1(a)] in ethanol (20 mL), under argon and at room temperature, was treated with sodium hydroxide solution (1 mL, 1M) and then heated at reflux temperature for 2.5 hours. The reaction mixture was evaporated to low volume (approximately 2 mL) and then treated with water (12 mL). This mixture was acidified to pH 1 by addition of hydrochloric acid (1.75 mL, 1M) and cooled in ice. The resulting solid was filtered, then washed three times with water (3 mL) and then dried at 60° C. under vacuum to give the title compound as a white solid. LC-MS: RT=3.53 minutes; MS (ES)=498 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2.5 hours
  3. customThe reaction mixture was evaporated to low volume (approximately 2 mL)
  4. additiontreated with water (12 mL)
  5. additionThis mixture was acidified to pH 1 by addition of hydrochloric acid (1.75 mL, 1M)
  6. temperaturecooled in ice
  7. filtrationThe resulting solid was filtered
  8. washwashed three times with water (3 mL)
  9. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-fdf3121b4e7b433db710db13f4b3d216
Source dataset
uspto-grants-2007_05
Patent number
US07211586B2

Reaction notes

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