Diisopropylethylamine → (1R,4R,5R)-N-[(1S)-1-[[[(1S)-1-Cyclohexyl-2-(methylamino)-2-oxoethyl]amino]carbonyl]-2,2-dimethylpropyl]-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide

HRID 2242450Notes

Reaction equation

HRID 2242450 reaction equation
[O:1]=[C:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][CH:6]2[C:9]([OH:11])=O)[O:3]1.[NH2:12][CH:13]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:14]([NH:16][CH:17]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:18](=[O:21])[NH:19][CH3:20])=[O:15].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:22]1([C@H:17]([NH:16][C:14]([C@@H:13]([NH:12][C:9]([C@@H:6]2[CH2:5][C@@H:4]3[CH2:8][C@H:7]2[C:2](=[O:1])[O:3]3)=[O:11])[C:28]([CH3:30])([CH3:29])[CH3:31])=[O:15])[C:18]([NH:19][CH3:20])=[O:21])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

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 462449653-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acidHCID 68491417HCID 68491417, compound

Product 1

HCID 68490886(1R,4R,5R)-N-[(1S)-1-[[[(1S)-1-Cyclohexyl-2-(methylamino)-2-oxoethyl]amino]carbonyl]-2,2-dimethylpropyl]-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamideYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 32 (53 mg, 0.34 mmol) in DMF (9 mL) was added compound 65 (80 mg, 0.28 mmol) and DIEA (290 □L, 1.66 mmol). The solution was cooled to 0° C. and HATU (127 mg, 0.33 mmol) was added. After stirring at 0° C. for 1 h and at rt for 1 h the solvent was evaporated, and the crude product was purified by flash column chromatography (EtOAc/toluene 2:1) to give compound 72 (110 mg, 92%) as a white solid.

Workup

  1. customwas evaporated
  2. customthe crude product was purified by flash column chromatography (EtOAc/toluene 2:1)

Sources & evidence

ORD record
ord-5ac40fb678a74f0492cbddac3de57f0a
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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