Triethylamine → (2S)-2-{[(S)-(4-bromophenyl)(thien-2-yl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide

HRID 1180385Notes

Reaction equation

HRID 1180385 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)[O:9][C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([OH:13])=O)=[CH:4][CH:3]=1.Cl.[NH2:24][CH2:25][C:26]#[N:27].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)[O:9][C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([NH:27][CH2:26][C:25]#[N:24])=[O:13])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11491918Aminoacetonitrile hydrochlorideHCID 69473998(2S)-2-{[(S)-(4-bromophenyl)(thien-2-yl)methyl]oxy}-4-methylpentanoic acid

Product 1

HCID 10342122(2S)-2-{[(S)-(4-bromophenyl)(thien-2-yl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S)-2-{[(S)-(4-bromophenyl)(thien-2-yl)methyl]oxy}-4-methylpentanoic acid from step 2, (273 mg, 0.71 mmol) in DMF (3.5 mL) was added aminoacetonitrile HCL salt (66 mg, 0.71 mmol), triethylamine (359 μL, 3.55 mmol) and HATU (270 mg, 0.71 mmol). The mixture was aged for 3 hours under a nitrogen atmosphere and was then poured into a saturated aqueous solution of NaHCO3. The resulting mixture was extracted 3 times with ethyl acetate. The organic extracts were washed with brine, dried and evaporated to a solid. The crude product was chromatographed on silica gel using 35% ethyl acetate in hexanes to afford the title compound.

Workup

  1. extractionThe resulting mixture was extracted 3 times with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. customdried
  4. customevaporated to a solid
  5. customThe crude product was chromatographed on silica gel using 35% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e05bd8d4e74543fcb9a0ecbf21daec60
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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