(Diethylamino)sulfur trifluoride → 1-[4-(1-Fluoro-ethyl)-3-(2-m-tolyl-ethoxy)-benzoylamino]-cycloheptanecarboxylic acid

HRID 1918297Notes

Reaction equation

HRID 1918297 reaction equation
C[O:2][C:3]([C:5]1([NH:12][C:13](=[O:33])[C:14]2[CH:19]=[CH:18][C:17]([C:20](=O)[CH3:21])=[C:16]([O:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[CH:15]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[BH4-].[Na+].C(N(S(F)(F)[F:42])CC)C>CO>[F:42][CH:20]([C:17]1[CH:18]=[CH:19][C:14]([C:13]([NH:12][C:5]2([C:3]([OH:2])=[O:4])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[O:33])=[CH:15][C:16]=1[O:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=1)[CH3:21]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 4311764Sodium borohydrideHCID 708721291-[4-Acetyl-3-(2-m-tolyl-ethoxy)-benzoylamino]-cycloheptanecarboxylic acid methyl ester

Product 1

HCID 671705281-[4-(1-Fluoro-ethyl)-3-(2-m-tolyl-ethoxy)-benzoylamino]-cycloheptanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound of step 2 of example 60 (110 mg, 0.244 mmol) was dissolved in methanol (1.1 ml) and cooled in an ice bath. Sodium borohydride (9.2 mg, 0.244 mmol) was added and stirring continued for 1 h. This mixture was partitioned between EA and saturated sodium hydrogencarbonate solution, the aqueous phase was extracted with EA, the combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue (100 mg) was dissolved in DCM (2 ml) and diethylaminosulfur trifluoride (36 mg, 0.22 mmol) was added. The mixture was stirred for 3 h, partitioned between EA and saturated sodium hydrogencarbonate solution, the aqueous phase was extracted with EA, the combined organic phases were dried over sodium sulfate and evaporated to dryness. The obtained ester was hydrolyzed in analogy to step 4 of example 1 to yield the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. customThis mixture was partitioned between EA and saturated sodium hydrogencarbonate solution
  3. extractionthe aqueous phase was extracted with EA
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. customevaporated to dryness
  6. dissolutionThe residue (100 mg) was dissolved in DCM (2 ml)
  7. stirringThe mixture was stirred for 3 h
  8. custompartitioned between EA and saturated sodium hydrogencarbonate solution
  9. extractionthe aqueous phase was extracted with EA
  10. dry with materialthe combined organic phases were dried over sodium sulfate
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-b07eb742f3ed41f7851c82c5ffa21730
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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