Diisopropylethylamine → HCID 172983304, compound

HRID 515653Notes

Reaction equation

HRID 515653 reaction equation
[CH2:1]1[S:5][C@@H:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[C@H:3]2[NH:14][C:15]([NH:17][C@@H:2]12)=[O:16].O[N:19]=[C:20]([NH2:36])[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:29]2[CH:30]=[C:31]([CH3:34])[CH:32]=[CH:33][C:28]=2[O:27][C:26]1=[O:35].CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C=O)C.ClCCl>[O:16]=[C:15]1[NH:17][C@H:2]2[CH2:1][S:5][C@@H:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]/[N:19]=[C:20](\[NH2:36])/[CH2:21][CH2:22][CH2:23][CH2:24][N:25]3[C:29]4[CH:30]=[C:31]([CH3:34])[CH:32]=[CH:33][C:28]=4[O:27][C:26]3=[O:35])=[O:12])[C@H:3]2[NH:14]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 446904HCID 446904, compoundHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 123617581HCID 123617581, compound

Product 1

HCID 172983304HCID 172983304, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of homobiotin 83 (10 mg, 0.039 mmol) and compound 13 (11 mg, 0.043 mmol) in anhydrous DMF (0.5 ml) was added EDCl (7 mg, 0.047 mmol) and DIPEA (6 mg, 0.045 mmol) and stirred under a nitrogen atmosphere at ambient temperature for 12 h. The reaction mixture was diluted with dichloromethane (25 ml) and washed with water (25 ml) and brine (25 ml). The organic layer was dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 19:1 dichloromethane/methanol to give a yellow oil (18 mg, 46%).

Workup

  1. washwashed with water (25 ml) and brine (25 ml)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 19:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-55d4529ce9d849b99e4515ef93061b8c
Source dataset
uspto-grants-2015_08
Patent number
US09108978B2

Reaction notes

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