Triethylamine → HCID 22121976, compound

HRID 1859360Notes

Reaction equation

HRID 1859360 reaction equation
Cl.[OH:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:33])[CH2:12][CH2:13][N:14]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:15]([CH:19]([CH3:21])[CH3:20])[C:16](O)=[O:17])[CH2:7][CH2:6]1.Cl.[CH2:35]([O:42][NH2:43])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(CC)CC)C.B(F)([O-])[O-].B(F)([O-])[O-].B(F)([O-])[O-].B(F)([O-])[O-].B(F)([O-])[O-].B(F)([O-])[O-].N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.CN(C)C=O>[CH2:35]([O:42][NH:43][C:16](=[O:17])[CH:15]([N:14]([CH2:13][CH2:12][C:11]([N:8]1[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][OH:2])[CH2:6][CH2:7]1)=[O:33])[S:22]([C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1)(=[O:24])=[O:23])[CH:19]([CH3:20])[CH3:21])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 102312Benzyloxyamine hydrochlorideHCID 70252504HCID 70252504, compoundHCID 86755729HCID 86755729, compound

Product 1

HCID 22121976HCID 22121976, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[{3-[4-(2-hydroxyethyl)piperazin-1-yl]-3-oxopropyl}(4-methoxy-benzenesulfonyl)amino]-3-methylbutyric acid hydrochloride (1.10 grams, 2.17 mmol) in methylene chloride (50 mL) and N,N-dimethylformamide (0.5 mL) were added sequentially O-benzylhydroxylamine hydrochloride (0.41 grams, 2.60 mmol), triethylamine (0.91 mL, 6.5 mmol) and (benzotriazol-1-yloxy)tris-(dimethylamino)-phosphonium hexafluoroborate (1.20 grams, 2.71 mmol). The resulting mixture was stirred for 16 hours at room temperature and then concentrated in vacuo. The residue was taken up in ethyl acetate and washed successively with saturated sodium bicarbonate solution, water and brine. The solution was dried over magnesium sulfate and concentrated to yield an oil which was chromatographed on silica gel eluting with 3% methanol in chloroform to afford N-benzyloxy-2-[{3-[4-(2-hydroxyethyl)piperazin-1-yl]-3-oxopropyl}(4-methoxybenzenesulfonyl)amino]-3-methylbutyramide as a clear oil (0.85 grams, 68%). Conversion to the hydrochloride salt was subsequently carried out using anhydrous hydrochloric acid in cold (0° C.) methylene chloride.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed successively with saturated sodium bicarbonate solution, water and brine
  3. dry with materialThe solution was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto yield an oil which
  6. customwas chromatographed on silica gel eluting with 3% methanol in chloroform

Sources & evidence

ORD record
ord-35b9277f06204c2d896737d7b0599d28
Source dataset
uspto-grants-2000_11
Patent number
US06153609

Reaction notes

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