Ammonium Chloride → (S)-t-Butyl 2-(2-(2-((tert-butyldiphenylsilyl)oxy)acetyl)hydrazinecarbonyl)pyrrolidine-1-carboxylate

HRID 710042

Reaction equation

HRID 710042 reaction equation
[NH:1]([C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4])[NH2:2].[Si:17]([O:34][CH2:35][C:36](O)=[O:37])([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[NH4+].[Cl-]>O.C(Cl)(Cl)Cl>[Si:17]([O:34][CH2:35][C:36]([NH:2][NH:1][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4])=[O:37])([C:30]([CH3:32])([CH3:33])[CH3:31])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10014050tert-Butyl (2S)-2-(hydrazinecarbonyl)pyrrolidine-1-carboxylateHCID 111415642-((tert-Butyldiphenylsilyl)oxy)acetic acid

Product 1

HCID 86706754(S)-t-Butyl 2-(2-(2-((tert-butyldiphenylsilyl)oxy)acetyl)hydrazinecarbonyl)pyrrolidine-1-carboxylateYield 61.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of CHCl3 (100 mL) with (S)-t-butyl 2-(hydrazinecarbonyl)pyrrolidine-1-carboxylate (4.791 g), 2-((t-butyldiphenylsilyl)oxy)acetic acid (6.28 g), WSC.HCl (4.371 g) and HOBt.H2O (3.081 g) was stirred at room temperature for 15 hours. To the reaction mixture, a saturated aqueous solution of NH4Cl (500 mL) was added, followed by extraction with AcOEt (500 mL). The organic layer was washed successively with saturated aqueous sodium bicarbonate (500 mL) and brine (500 mL), dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (6.42 g, colorless amorphous.)

Workup

  1. extractionfollowed by extraction with AcOEt (500 mL)
  2. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate (500 mL) and brine (500 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product, which
  7. customwas further purified by silica gel chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-e8a1dea0fe524084abffffd8048bbc51
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Linked notes

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