N'-Hydroxybenzenecarboximidamide → HCID 178452022, compound

HRID 1477750Notes

Reaction equation

HRID 1477750 reaction equation
C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH3:34][C:35]([O:38][C:39]([N:41]1[C@H:44]([C:45]([OH:47])=[O:46])[CH2:43][CH2:42]1)=[O:40])([CH3:37])[CH3:36].CCN(C(C)C)C(C)C.O[N:58]=[C:59]([NH2:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>C(Cl)Cl.O>[C:59](=[NH:58])([NH:66][O:46][C:45]([C@@H:44]1[CH2:43][CH2:42][N:41]1[C:39]([O:38][C:35]([CH3:34])([CH3:36])[CH3:37])=[O:40])=[O:47])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

7

Reactant 4

HCID 69186N'-HydroxybenzenecarboximidamideHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 2734495(2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acid

Product 1

HCID 178452022HCID 178452022, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

PyBOP (2.53 g, 4.85 mmol) was added to a 0° C. solution of Boc-L-azetidine-2-carboxylic acid (650 mg, 3.23 mmol) and DIPEA (1.66 mL, 9.69 mmol) in DCM (14 mL) and the rxn mixture was stirred at rt for 20 min, before N′-hydroxybenzimidamide (440 mg, 3.23 mmol) was added and stirring continued at rt for 2 h. To the rxn mixture was added H2O and the mixture extracted with DCM (2×). The combined org. extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to yield (S)-tert-butyl 2-((benzimidamidooxy)carbonyl)azetidine-1-carboxylate B-1-1 which was used further without purification.

Workup

  1. additionwas added
  2. extractionthe mixture extracted with DCM (2×)
  3. washextracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-853a790f0629469db78228c2cbd44feb
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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