Triethylamine → Ammonia

HRID 1866561Notes

Reaction equation

HRID 1866561 reaction equation
[Si:1]([O:8][C@H:9]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH2:32][OH:33])[CH:26]=1)[CH2:10][NH:11][C:12]([CH3:24])([CH3:23])[CH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([OH:19])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[Cl:65][C:66]1[CH:67]=[CH:68][C:69]([O:75][CH3:76])=[C:70]([CH2:72][CH2:73][NH2:74])[CH:71]=1>CN(C)C(=O)C>[NH3:11].[Si:1]([O:8][C@H:9]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH2:32][OH:33])[CH:26]=1)[CH2:10][NH:11][C:12]([CH3:23])([CH3:24])[CH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([NH:74][CH2:73][CH2:72][C:70]1[CH:71]=[C:66]([Cl:65])[CH:67]=[CH:68][C:69]=1[O:75][CH3:76])=[O:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 209848495-Chloro-2-methoxybenzeneethanamineHCID 579783093-{2-[(2R)-2-(tert-butyldimethyl silanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid

Product 2

HCID 222AmmoniaHCID 690233563-[2-({(2R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)-2-methylpropyl]-N-[2-(5-chloro-2-methoxyphenyl)ethyl]benzamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 3-{2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxy methylphenyl)ethylamino]-2-methylpropyl}benzoic acid (preparation 37) (400 mg, 0.85 mmol), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (320 mg, 0.85 mmol), triethylamine (225 μL, 1.6 mmol) and 2-(5-chloro-2-methoxy-phenyl)-ethylamine (preparation 70), (64 mg, 0.85 mmol) in N,N-dimethylacetamide (8 mL) was stirred for 18 hours at room temperature. The solvent was removed in vacuo and the residue was partitioned between dichloromethane (4 mL) and saturated sodium hydrogen carbonate solution (1 mL). The organic solution was then dried over magnesium sulfate, concentrated in vacuo and the residue was purified using an ISCO Companion® silica cartridge, eluting with dichloromethane:methanol:0.88 ammonia, 90:10:1 to 80:20:2, to afford the title compound in 22% yield.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between dichloromethane (4 mL) and saturated sodium hydrogen carbonate solution (1 mL)
  3. dry with materialThe organic solution was then dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-d589937ccd834c09bdc44c1bcf609949
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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