Diisopropylethylamine → HCID 86596943, compound

HRID 2225239Notes

Reaction equation

HRID 2225239 reaction equation
[CH2:1]([C@H:5]1[C@@H:10]([NH2:11])[CH2:9][CH2:8][C@@H:7]([N:12]([CH:14]([CH3:16])[CH3:15])[CH3:13])[CH2:6]1)[CH2:2][CH2:3][CH3:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:41]([NH:48][C@@H:49]([C:51](O)=[O:52])[CH3:50])([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42].C(N(CC)C(C)C)(C)C>CN(C=O)C.C(Cl)Cl>[CH2:1]([C@@H:5]1[CH2:6][C@H:7]([N:12]([CH:14]([CH3:15])[CH3:16])[CH3:13])[CH2:8][CH2:9][C@@H:10]1[NH:11][C:51](=[O:52])[C@H:49]([NH:48][C:41](=[O:42])[O:43][C:44]([CH3:46])([CH3:45])[CH3:47])[CH3:50])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 637606BOC-D-alanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69287214HCID 69287214, compound

Product 1

HCID 86596943HCID 86596943, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

A solution of (1R,3R,4S)-3-butyl-N1-isopropyl-N1-methylcyclohexane-1,4-diamine (81 mg, 0.35 mmol; see Example 3a, Step 4) in 1:1 DMF/methylene chloride (5 mL) was charged successively with HATU (162 mg, 0.43 mmol), N-Boc D-Alanine (67 mg, 0.35 mmol), and N,N-diisopropylethylamine (0.31 mL, 1.77 mmol). The reaction was stirred for 16 h at RT, concentrated in vacuo, and diluted with EtOAc. The organic phase was washed successively with sat. NaHCO3, water, 1N HCl, water, and brine before being dried (sodium sulfate), filtered, and concentrated in vacuo to afford tert-butyl (R)-1-((1S,2R,4R)-2-butyl-4-(isopropyl(methyl)amino)cyclohexylamino)-1-oxopropan-2-ylcarbamate. MS found: (M+H)+=398.4.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with EtOAc
  3. washThe organic phase was washed successively with sat. NaHCO3, water, 1N HCl, water, and brine
  4. dry with materialbefore being dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31c5f10346324373be803b88f7688224
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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