benzyl 3-[(E)-C-(3,3-dimethoxypropyl)-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbonimidoyl]azetidine-1-carboxylate → benzyl 3-(1-[(tert-butoxycarbonyl)amino]-1H-pyrrol-2-yl}azetidine-1-carboxylate

HRID 1972943Notes

Reaction equation

HRID 1972943 reaction equation
[C:1]([O:5][C:6]([NH:8]/[N:9]=[C:10](/[CH:18]1[CH2:21][N:20]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:19]1)\[CH2:11][CH2:12][CH:13](OC)OC)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6]([NH:8][N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH:18]1[CH2:21][N:20]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:19]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 58529451benzyl 3-[(E)-C-(3,3-dimethoxypropyl)-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbonimidoyl]azetidine-1-carboxylate

Product 1

HCID 58529958benzyl 3-(1-[(tert-butoxycarbonyl)amino]-1H-pyrrol-2-yl}azetidine-1-carboxylateYield 99.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of benzyl 3-[(1E)-N-(tert-butoxycarbonyl)-4,4-dimethoxybutanehydrazonoyl]azetidine-1-carboxylate (2.47 g, 5.67 mmol) and AcOH (30 mL) was stirred (40° C.) for 18 h. The mixture was concentrated and the residue was dissolved in EtOAc (75 mL) and washed with saturated, aqueous NaHCO3 (75 mL). The aqueous layer was extracted with EtOAc (2×50 mL) and the combined organic layers were washed with brine, dried (Na2SO4) and concentrated to afford the desired product (2.1 g) which was used without further purification. ES-MS m/z 272.01 [M+H]+, HPLC RT (min) 3.50.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in EtOAc (75 mL)
  3. washwashed with saturated, aqueous NaHCO3 (75 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6ce4edb856f844cfaa05762b2453013f
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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