Sodium Hydroxide → HCID 10301294, compound

HRID 1375069Notes

Reaction equation

HRID 1375069 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][C:5]1([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:38])[CH2:19][C:20]3[CH:36]=[C:35]([CH3:37])[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>[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]([NH:17][C:14]2[CH:15]=[CH:16][C:11]([C:5]3([CH2:4][C:3]([OH:39])=[O:2])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)=[CH:12][CH:13]=2)=[O:38])[CH:36]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69418526HCID 69418526, compound

Product 1

HCID 10301294HCID 10301294, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (4-(4-{2-[4-methyl-2-o-tolylamino-benzoxazol-6-yl]-acetylamino}-phenyl)-tetrahydro-pyran-4-yl)-acetic acid methyl ester [0.178 g, Reference Example 17(a)] in degassed ethanol (30 mL) was treated with sodium hydroxide solution (1 mL, 1N) and the mixture was stirred under nitrogen and at reflux temperature for 6 hours. The resulting red solution was evaporated and the residue was subjected to preparative HPLC on a Hypersil Elite C18 column eluting initially with a mixture of acetonitrile, water and trifluoroacetic acid (25:75:0.1, v/v/v) and then 1% acetonitrile/minute gradient to give the title compound (0.052 g) as a solid. LC-MS: RT=3.30 minutes, MS(ES+): 514.06(M+H)+; MS(ES−): 512.08(M−H)−.

Workup

  1. temperatureat reflux temperature for 6 hours
  2. customThe resulting red solution was evaporated
  3. washeluting initially with a mixture of acetonitrile, water and trifluoroacetic acid (25:75:0.1, v/v/v)

Sources & evidence

ORD record
ord-7dd485c1577c48d39c38b9b2f3125a26
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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