Isopropyl Acetate → HCID 59543587, compound

HRID 1697555Notes

Reaction equation

HRID 1697555 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:19][C:18]=3[C:29]([F:32])([F:31])[F:30])(=[O:16])=[O:15])[CH2:11][NH:10]2)=[O:8])[CH2:5][CH2:4]1)#[N:2].[F:33][C:34]([F:42])([F:41])[C:35]1([C:38](O)=[O:39])[CH2:37][CH2:36]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(OC(C)=O)(C)C>CN(C=O)C>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:26])([F:27])[F:28])=[CH:19][C:18]=3[C:29]([F:31])([F:32])[F:30])(=[O:16])=[O:15])[CH2:11][N:10]2[C:38]([C:35]2([C:34]([F:42])([F:41])[F:33])[CH2:37][CH2:36]2)=[O:39])=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

7

Reactant 5

HCID 7915Isopropyl AcetateHCID 81531DiisopropylethylamineHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86646818HCID 86646818, compound

Product 1

HCID 59543587HCID 59543587, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S,4R)-4-[4-(2,2,2-Trifluoro-ethoxy)-2-trifluoromethyl-benzenesulfonyl]-pyrrolidine-2-carboxylic acid (1-cyano-cyclopropyl)-amide (20 mg, 41 umol; example 211a) was dissolved in DMF (0.4 ml) under a N2-atmosphere at ambient temperature. 1-Trifluoromethyl-cyclopropanecarboxylic acid (10 mg, 62 umol; CAS Reg. No. 277756-46-4), HATU (23 mg, 62 umol) and DIEA (10 ul, 62 umol) were added and the reaction mixture was stirred for 48 h at ambient temperature. Ice water/brine 1/1 and iPrOAc were added and the layers were separated. The aqueous layer was extracted one more time with iPrOAc, the combined organic layers were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure to give a yellow oil which was purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane) to obtain the title compound (13 mg, 21 umol; 51%) as colorless solid. MS (ESI): m/z=622.3 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted one more time with iPrOAc
  3. washthe combined organic layers were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customto give a yellow oil which
  7. customwas purified by preparative thin layer chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-8742c51a00d34805a730b5bdcd842f14
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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