Diisopropylethylamine → tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-methoxycarbonylethyl)benzoylamino)propionate

HRID 984031Notes

Reaction equation

HRID 984031 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)=[O:4].[CH2:16]([O:23][C:24]([NH:26][C@@H:27]([CH2:35][NH2:36])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.F[B-](F)(F)F.C(C(=NOC(N(C)C)=[N+](C)C)C(OCC)=O)#N.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH2:16]([O:23][C:24]([NH:26][C@@H:27]([CH2:35][NH:36][C:11](=[O:13])[C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[CH:15][CH:14]=1)[C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 10803731(S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoateHCID 113102944-(3-Methoxy-3-oxopropyl)benzoic acid

Product 1

HCID 15512203tert-butyl (2S)-2-benzyloxycarbonylamino-3-(4-(2-methoxycarbonylethyl)benzoylamino)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

354 mg (1.7 mmol) of 4-(2-methoxycarbonylethyl)benzoic acid (step b) and 500 mg (1.7 mmol) of tert-butyl (2S)-2-benzyloxycarbonylamino-3-aminopropionate were dissolved in 3 ml of dimethylformamide and treated with 557 mg (1.7 mmol) of O-((cyano(ethoxycarbonyl)methylene)amino)-1,1,3,3-tetramethyluronium tetrafluoroborate (TOTU) and 204 mg (1.7 mmol) of diisopropylethylamine and the solution was stirred at room temperature for 7 h. The solvent was evaporated in vacuo, the residue was dissolved in ethyl acetate and washed three times each with a solution of potassium hydrogen sulfate and a solution of sodium bicarbonate until neutral. The organic phase was separated off and dried, and the solvent was distilled off in vacuo. Yield: 770 mg (93%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed three times each with a solution of potassium hydrogen sulfate
  4. customThe organic phase was separated off
  5. customdried
  6. distillationthe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-65b81d23378f484dab000bba92fb41d7
Source dataset
uspto-grants-2005_03
Patent number
US06867213B2

Reaction notes

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