Diisopropylethylamine → HCID 136381317, compound

HRID 1045389Notes

Reaction equation

HRID 1045389 reaction equation
[O:1]=[S:2]1(=[O:23])[C:8]2[CH:9]=[C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([OH:19])=O)[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][NH:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[OH:55][NH:56][C:57](=[NH:59])[CH3:58]>C(Cl)Cl>[O:23]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([NH:59]/[C:57](=[N:56]\[OH:55])/[CH3:58])=[O:19])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][NH:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66791293HCID 66791293, compoundHCID 178465666HCID 178465666, compound

Product 1

HCID 136381317HCID 136381317, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of the product obtained in Step A above (540 mg, 1.61 mmol) in 10 ml of CH2Cl2 there are added, in succession, 516 mg (1.61 mmol) of TBTU and then 364 μl (2.09 mmol) of DIEA. After stirring for 20 minutes, 120 mg (1.61 mmol) of N-hydroxyacetamidine are added and the reaction mixture is stirred for 1.5 hours at ambient temperature. The reaction mixture is washed with water and then with saturated NaCl solution, dried (MgSO4) and evaporated to dryness. The residue is taken up in CH2Cl2; a white precipitate forms which is filtered off to yield the expected product.

Workup

  1. stirringthe reaction mixture is stirred for 1.5 hours at ambient temperature
  2. washThe reaction mixture is washed with water
  3. dry with materialwith saturated NaCl solution, dried (MgSO4)
  4. customevaporated to dryness
  5. filtrationa white precipitate forms which is filtered off

Sources & evidence

ORD record
ord-87824c56d6d7446589e608b66b218fa2
Source dataset
uspto-grants-2013_10
Patent number
US08569285B2

Reaction notes

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