Diisopropylethylamine → HCID 67514413, compound

HRID 1965198Notes

Reaction equation

HRID 1965198 reaction equation
[CH:1]([NH:4][C:5]([N:7]1[CH2:11][CH:10]([OH:12])[CH:9]2[N:13]([C:16](=[O:23])[CH:17]([NH2:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:14][CH2:15][CH:8]12)=[O:6])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[C:33]([N:43]([CH3:49])[C@H:44]([C:46](O)=[O:47])[CH3:45])([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C)[C@H](C(O)=O)C)(OCC1C=CC=CC=1)=O>CN1C(=O)CCC1.O>[CH2:36]([O:35][C:33](=[O:34])[N:43]([CH:44]([C:46](=[O:47])[NH:22][CH:17]([C:16]([N:13]1[CH2:14][CH2:15][CH:8]2[N:7]([C:5](=[O:6])[NH:4][CH:1]([CH3:3])[CH3:2])[CH2:11][CH:10]([OH:12])[CH:9]12)=[O:23])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:45])[CH3:49])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

8

Reactant 5

HCID 81531Diisopropylethylamine2×HCID 7016365Z-N-Me-Ala-OHHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67609205HCID 67609205, compound2×HCID 131730510HCID 131730510, compound

Product 1

HCID 67514413HCID 67514413, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution containing 56 (5.10 g, 15.6 mmol) and DIPEA (3.6 mL, 20.3 mmol) in NMP (20 mL) was cooled to 0° C. In a separate flask at 0° C., Cbz-N(Me)Ala-OH (4.1 g, 17.2 mmol), HATU (6.6 g, 17.2 mmol), and DIPEA (3.6 mL, 20.3 mmol) were dissolved in NMP (80 mL). A portion of the HATU/Cbz-N(Me)Ala-OH solution (72 mL, ˜1.0 equiv) was then added to the cooled solution of 56. After 45 min, the reaction mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed successively with 10% H3PO4, water, saturated aqueous NaHCO3, water, and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 7.0 g (82%, 2 steps) of 57 as a white foam. Mass spectrum, m/z [546.0] (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed successively with 10% H3PO4, water, saturated aqueous NaHCO3, water, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-69598a1f841742e287e443a01a755112
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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