Sodium Hydroxide → HCID 10278603, compound

HRID 1375070Notes

Reaction equation

HRID 1375070 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:37])[CH2:19][C:20]3[CH:36]=[CH:35][C:23]4[N:24]=[C:25]([NH:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=5[CH3:34])[O:26][C:22]=4[CH:21]=3)=[CH:13][CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[OH-].[Na+]>C(O)C>[C:29]1([CH3:34])[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[NH:27][C:25]1[O:26][C:22]2[CH:21]=[C:20]([CH2:19][C:18]([NH:17][C:14]3[CH:15]=[CH:16][C:11]([C:5]4([CH2:4][C:3]([OH:38])=[O:2])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]4)=[CH:12][CH:13]=3)=[O:37])[CH:36]=[CH:35][C:23]=2[N:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69420721HCID 69420721, compound

Product 1

HCID 10278603HCID 10278603, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (4-(4-{2-[2-o-tolylamino-benzoxazol-6-yl]-acetylamino}-phenyl)-tetrahydro-pyran-4-yl)-acetic acid methyl ester [0.2 g, Reference Example 17(b)] in ethanol (25 mL) was treated with sodium hydroxide solution (2 mL, 1N) and the mixture was stirred under argon and at reflux temperature for 3 hours. The reaction mixture was evaporated and the residue was dissolved in water (25 mL). This solution was washed with diethyl ether (10 mL) and then acidified to pH 1 by addition of hydrochloric acid (3 mL, 1N). The resulting precipitate was filtered, then washed four times with water (5 mL) and then dried at 60° C. under high vacuum to give the title compound (0.1 g) as an off-white solid. LC-MS: RT=3.10 minutes, MS(ES+): 500(M+H)+.

Workup

  1. temperatureat reflux temperature for 3 hours
  2. customThe reaction mixture was evaporated
  3. dissolutionthe residue was dissolved in water (25 mL)
  4. washThis solution was washed with diethyl ether (10 mL)
  5. additionacidified to pH 1 by addition of hydrochloric acid (3 mL, 1N)
  6. filtrationThe resulting precipitate was filtered
  7. washwashed four times with water (5 mL)
  8. customdried at 60° C. under high vacuum

Sources & evidence

ORD record
ord-c76c357f914d4a6d8037e184bbf0aac5
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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