Triethylamine → HCID 12149178, compound

HRID 916065Notes

Reaction equation

HRID 916065 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@H:12]([CH3:24])[CH2:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21](O)=[O:22])[CH:17]=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.[CH3:64][O:65][C:66]1[CH:73]=[CH:72][CH:71]=[C:70]([O:74][CH3:75])[C:67]=1[CH2:68][NH2:69]>CN(C)C=O>[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@H:12]([CH3:24])[CH2:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([NH:69][CH2:68][C:67]2[C:70]([O:74][CH3:75])=[CH:71][CH:72]=[CH:73][C:66]=2[O:65][CH3:64])=[O:22])[CH:17]=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28008722,6-DimethoxybenzylamineHCID 58959819(3-{(2R)-2-[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethylamino]-propyl}-phenyl)-acetic acidHCID 178526939HCID 178526939, compound

Product 2

HCID 222AmmoniaHCID 12149178HCID 12149178, compoundYield 128.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (3-{(2R)-2-[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethylamino]-propyl}-phenyl)-acetic acid (Preparation 36) (150 mg, 0.32 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (67 mg, 0.35 mmol), hydroxybenzotriazole monohydrate (47 mg, 0.35 mmol) in N,N-dimethylformamide (3 ml) was treated with triethylamine (0.09 ml, 0.63 mmol) and 2,6-dimethoxybenzylamine (58 mg, 0.35 mmol) and the resulting suspension left to stir at room temperature under a nitrogen atmosphere for 18 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (10 ml) and saturated aqueous sodium bicarbonate (10 ml). The organic phase was separated, and the aqueous phase extracted with further ethyl acetate (2×10 ml). The combined organic extracts were washed with water (5 ml), brine (5 ml), dried (sodium sulphate) and the solvent removed in vacuo. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol: 880 ammonia (95:5:0.5 by volume) to give the title compound as a pale yellow oil (128 mg).

Workup

  1. waitthe resulting suspension left
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between ethyl acetate (10 ml) and saturated aqueous sodium bicarbonate (10 ml)
  4. customThe organic phase was separated
  5. extractionthe aqueous phase extracted with further ethyl acetate (2×10 ml)
  6. washThe combined organic extracts were washed with water (5 ml), brine (5 ml)
  7. dry with materialdried (sodium sulphate)
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-a6dcda7794994ca29ccca05ecbea4abe
Source dataset
uspto-grants-2007_09
Patent number
US07268147B2

Reaction notes

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