Diisopropylethylamine → 2,3-difluoro-N-[2-({(1R)-3-methyl-1-[(3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl} amino)-2-oxoethyl]benzamide

HRID 539590Notes

Reaction equation

HRID 539590 reaction equation
[F:1][C:2]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][C:8]([OH:10])=O)=[O:5].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:38][CH:39]([CH3:56])[CH2:40][C@@H:41]([B:43]1[O:47][C@@H:46]2[CH2:48][C@@H:49]3[CH2:52][C@H:51]([C@:45]2([CH3:55])[O:44]1)[C:50]3([CH3:54])[CH3:53])[NH2:42].FC(F)(F)C([O-])=O.CCN(C(C)C)C(C)C>CN(C)C=O>[F:1][C:2]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:42][C@H:41]([B:43]1[O:47][C@H:46]2[CH2:48][C@H:49]3[CH2:52][C@@H:51]([C@@:45]2([CH3:55])[O:44]1)[C:50]3([CH3:53])[CH3:54])[CH2:40][CH:39]([CH3:56])[CH3:38])=[O:10])=[O:5]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 84468TrifluoroacetateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 44244714(R)-3-Methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butan-1-amineHCID 59816243[(2,3-Difluorobenzoyl)amino]acetic acid

Product 1

HCID 673690412,3-difluoro-N-[2-({(1R)-3-methyl-1-[(3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl} amino)-2-oxoethyl]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [(2,3-difluorobenzoyl)amino]acetic acid (0.205 g, 0.95 mmol) in dimethylformamide (10 mL) were added TBTU (0.337 g, 1.0 mmol) and (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butan-1-amine as its trifluoroacetate salt (0.362 g, 0.95 mmol). The mixture was allowed to cool to 0° C. and DIEA (0.498 mL, 2.9 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with water (100 mL) and the product partitioned into DCM. The organic layer was dried over sodium sulfate and the solvent removed to give 2,3-difluoro-N-[2-({(1R)-3-methyl-1-[(3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamide.

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched with water (100 mL)
  3. customthe product partitioned into DCM
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent removed

Sources & evidence

ORD record
ord-676887b045f54d038a7dd98b5877e0cc
Source dataset
uspto-grants-2014_10
Patent number
US08871745B2

Reaction notes

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