Diisopropylethylamine → HCID 15895101, compound

HRID 1953045Notes

Reaction equation

HRID 1953045 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:10][C@@H:9]1[C:22](O)=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N([CH:31]([CH3:33])[CH3:32])CC)(C)C.Cl.[CH2:35]([O:42][NH2:43])C1C=CC=CC=1.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)[C:72]2C=CC=[CH:76][C:71]=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>[C:1]([O:5][C:6]([N:8]1[C@@H:9]([C:22](=[O:23])[NH:43][O:42][CH2:35][C:32]2[CH:31]=[CH:33][CH:76]=[CH:71][CH:72]=2)[CH2:10][C@@H:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[C:12]1=[O:13])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 102312Benzyloxyamine hydrochlorideHCID 10735516HCID 10735516, compoundHCID 86755729HCID 86755729, compound

Product 1

HCID 15895101HCID 15895101, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R, 4S)-4-(4-methoxyphenyl)-5-oxopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (305 mg, 0.91 mmol), diisopropylethylamine (0.35 mL, 2.0 mmol) and O-benzylhydroxylamine hydrochloride (160 mg, 1.0 mmol) in methylene chloride (20 mL) was added (benztriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluoroborate (443 mg, 1.0 mmol). The reaction was stirred at room temperature overnight. After dilution with methylene chloride, the mixture was washed with aqueous saturated sodium bicarbonate solution, water and brine. The solution was dried over magnesium sulfate and concentrated to a white solid from which the title compound (294 mg, 73%) was isolated by flash chromatography eluting with 25% hexane in ethyl acetate.

Workup

  1. washAfter dilution with methylene chloride, the mixture was washed with aqueous saturated sodium bicarbonate solution, water and brine
  2. dry with materialThe solution was dried over magnesium sulfate
  3. concentrationconcentrated to a white solid from which the title compound (294 mg, 73%)
  4. customwas isolated by flash chromatography
  5. washeluting with 25% hexane in ethyl acetate

Sources & evidence

ORD record
ord-946b03de09e2416d95578084d658a897
Source dataset
uspto-grants-2000_09
Patent number
US06114361

Reaction notes

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