Triphenylphosphine → 1-{3-[2-(5-Chloro-2-fluoro-phenyl)-ethoxy]-4-methoxy-benzoylamino}-cycloheptanecarboxylic acid methyl ester

HRID 1475694Notes

Reaction equation

HRID 1475694 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:12][C:13](=[O:23])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([OH:22])[CH:15]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:43][C:44]1[CH:45]=[CH:46][C:47]([F:53])=[C:48]([CH2:50][CH2:51]O)[CH:49]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([NH:12][C:13](=[O:23])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:51][CH2:50][C:48]3[CH:49]=[C:44]([Cl:43])[CH:45]=[CH:46][C:47]=3[F:53])[CH:15]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 670764502-(5-Chloro-2-fluorophenyl)ethan-1-olHCID 67170485HCID 67170485, compound

Product 1

HCID 671689841-{3-[2-(5-Chloro-2-fluoro-phenyl)-ethoxy]-4-methoxy-benzoylamino}-cycloheptanecarboxylic acid methyl esterYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of step 2 (80 mg, 0.249 mmol) and triphenylphosphine (98 mg, 0.374 mmol) were dissolved in THF. 2-(5-Chloro-2-fluoro-phenyl)-ethanol (48 mg, 0.274 mmol) and DIAD (80.3 mg, 0.374 mmol) were added and the mixture was stirred at room temperature for 2 h. The volatiles were evaporated in vacuo and the residue was purified by preparative RP HPLC (water/ACN gradient) to give 85 mg of the title compound.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customthe residue was purified by preparative RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-0a0c59e5886c4ff29169d70a1350d8c8
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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