Water → HCID 10113955, compound

HRID 1070398Notes

Reaction equation

HRID 1070398 reaction equation
C[Si](C)(C)CC[O:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[NH:18][C:19]([O:21][CH2:22][C:23]1[O:24][C:25]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:28][C:26]=2[CH:27]=1)=[O:20])=[O:7].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>CN(C=O)C>[C:32]1([C:29]2[CH:30]=[CH:31][C:25]3[O:24][C:23]([CH2:22][O:21][C:19]([NH:18][C:9]4[CH:10]=[CH:11][C:12]5[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=5)[C:8]=4[C:6]([OH:7])=[O:5])=[O:20])=[CH:27][C:26]=3[CH:28]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 69687430HCID 69687430, compound

Product 1

HCID 10113955HCID 10113955, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 2-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (574 mg, 1.07 mmol) in DMF (5 mL) was added 1.0M tetra-n-butylammonium fluoride (1.1 mL, 1.07 mmol) under a nitrogen atmosphere. The mixture was stirred for 1.5 h. Water was added and the mixture was extracted, washed with water and brine, dried and concentrated to ca. 3 mL. The suspension was cooled at 0-5° C. for 40 min and filtered. Recrystallization of the obtained white solid gave 224 mg of 2-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-naphthalene-1-carboxylic acid, 201, mp: 174.5-177.2° C.

Workup

  1. extractionthe mixture was extracted
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated to ca. 3 mL
  5. filtrationfiltered
  6. customRecrystallization of the obtained white solid

Sources & evidence

ORD record
ord-9a448cacbacf4eeb895e3b3900799a4e
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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