Water → 4-[4-[6-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophen-2-yl]phenoxy]butanol Oxalate

HRID 1595050Notes

Reaction equation

HRID 1595050 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[C:20]([O:30][CH3:31])[CH:19]=3)=[C:15]([C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=3)[S:14][C:13]=2[CH:39]=1)C1C=CC=CC=1.C[O:41][C:42](=[O:47])[CH2:43][CH2:44][CH2:45]Cl.[C:48]([O-:51])([O-:50])=O.[Cs+].[Cs+].O>CN(C=O)C>[C:42]([OH:47])(=[O:41])[C:48]([OH:51])=[O:50].[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[C:20]([O:30][CH3:31])[CH:19]=3)=[C:15]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:45][CH2:44][CH2:43][CH2:42][OH:41])=[CH:34][CH:33]=3)[S:14][C:13]=2[CH:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 76612Butanoic acid, 4-chloro-, methyl esterHCID 22462686HCID 22462686, compound

Product 1

HCID 217063434-[4-[6-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophen-2-yl]phenoxy]butanol Oxalate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-[6-Benzyloxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]benzo[b]thiophen-2-yl]phenol (0.10 g; 0.19 mmol), 4-chlorobutyric acid methyl ester (27 mL; 0.22 mmol) and Cs2CO3 (0.43 g; 1.31 mmol) were combined in 2 mL of DMF and heated in an oil bath maintained at 80° C. for 3 h. After cooling to room temperature, water (30 mL) was added, and extraction was carried out with EtOAc (4×25 mL). The combined organics were washed with brine and dried by passage through Na2SO4. Purification was effected by flash chromatography on silica gel, eluting with EtOAc(100-90%)/Et3N(0-5%)/MeOH(0-5%). The title product was obtained as a colorless oil (92 mg, 78%).

Workup

  1. temperatureheated in an oil bath
  2. temperatureAfter cooling to room temperature
  3. extractionextraction
  4. washThe combined organics were washed with brine
  5. dry with materialdried by passage through Na2SO4
  6. customPurification
  7. washeluting with EtOAc(100-90%)/Et3N(0-5%)/MeOH(0-5%)

Sources & evidence

ORD record
ord-91e8fad291484c40aa3eca236cb2168b
Source dataset
uspto-grants-2001_09
Patent number
US06284756B1

Reaction notes

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