Acetonitrile → Tert-butyl 3-hydrazinylpropanoate

HRID 582686Notes

Reaction equation

HRID 582686 reaction equation
Cl.[NH2:2][CH2:3][C@H:4](NS(C1C=CC=CC=1)(=O)=O)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].F[P-](F)(F)(F)(F)F.[N:29]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.CC#N>C(OCC)(=O)C>[C:8]([O:7][C:5](=[O:6])[CH2:4][CH2:3][NH:2][NH2:29])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochloride

Product 1

HCID 11040997Tert-butyl 3-hydrazinylpropanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of acid 2-7 (380 mg, 1.19 mmole), amine 1-4 (362 mg, 1.19 mmole), BOP (789 mg, 1.79 mmole), NMM (521 μl, 4.76 mmole) and CH3CN (6 ml) was stirred at ambient temperature for 20 h. The reaction was diluted with ethyl acetate and then washed with H2O, sat. NaHCO3, 10% KHSO4, brine, dried (MgSO4) and concentrated. Flash chromotography (silica, EtOAc) gave the ester 2-8 as a white solid.

Workup

  1. washwashed with H2O, sat. NaHCO3, 10% KHSO4, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-377dd23692be4b98a357a7e8ec328630
Source dataset
uspto-grants-1999_07
Patent number
US05925655

Reaction notes

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