Diisopropylethylamine → HCID 131728746, compound

HRID 602102Notes

Reaction equation

HRID 602102 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=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.[NH2:50][C@H:51]1[C@@H:55]([OH:56])[CH2:54][N:53]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[CH2:52]1>CN(C=O)C>[C:60]([O:59][C:57]([N:53]1[CH2:54][C@H:55]([OH:56])[C@H:51]([NH:50][C:12]([C:11]2[CH:10]=[N:9][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[CH:16][CH:15]=2)=[O:14])[CH2:52]1)=[O:58])([CH3:63])([CH3:61])[CH3:62]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 247299726-(3-Fluorophenyl)nicotinic acidHCID 50986390Cis-(3R, 4S)-1-Boc-3-aMino-4-hydroxypyrrolidine

Product 1

HCID 131728746HCID 131728746, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(3-fluorophenyl)nicotinic acid (391 mg, 1.8 mmol ) in DMF (10 mL) at 0° C. was added HATU (753 mg, 1.98 mmol) and DIPEA (0.47 mL, 2.07 mmol ). After 15 min, cis-tert-butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate was added and the reaction stirred at room temperature for 5 hrs. The solvent was removed in vacuo and the residue diluted with ethyl acetate and water. The layers were separated and the organic layer washed with brine, dried (MgSO4) and the solvent removed to give an oil, which after chromatography (silica, 65% ethyl acetate:hex) to give the desired product, cis-tert-butyl-3-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)-4-hydroxypyrrolidine-1-carboxylate (420 mg, 58%). LC/MS (M+H)=401.9 observed, 402.18 expected.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue diluted with ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic layer washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed
  7. customto give an oil, which after chromatography (silica, 65% ethyl acetate:hex)

Sources & evidence

ORD record
ord-e3a1b6b92c944483992250271f65838f
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Reaction notes

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