Benzylamine → HCID 59263905, compound

HRID 644982Notes

Reaction equation

HRID 644982 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)C.[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CO>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15](=[O:17])[NH:35][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:18][CH:19]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 521913N,N-Diethyl-2-propanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 166409054-(2-{[(Tert-butoxy)carbonyl]amino}ethyl)benzoic acid

Product 1

HCID 59263905HCID 59263905, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-(2-tert-Butoxycarbonylaminoethyl)benzoic acid (0.307 g) was dissolved in methanol (5 mL) and treated with diethylisopropylamine (0.605 mL) and benzylamine (0.379 mL). The mixture was cooled (0° C.) then HATU (1.32 g) was added in portions. The reaction mixture was stirred for 48 h at room temperature, then partially concentrated in vacuo and partitioned between 2M aqueous hydrochloric acid and ethyl acetate. The organic layer was washed with further aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, water, saturated aqueous sodium chloride, then dried (Na2SO4) and concentrated to afford a colourless oil (>0.41 g) which was used in the next step without further purification.

Workup

  1. concentrationpartially concentrated in vacuo
  2. custompartitioned between 2M aqueous hydrochloric acid and ethyl acetate
  3. washThe organic layer was washed with further aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, water, saturated aqueous sodium chloride
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9dc418872e034eb1a460bd3e8cb19109
Source dataset
uspto-grants-2010_04
Patent number
US07700782B2

Reaction notes

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