1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67076923, compound

HRID 1348586Notes

Reaction equation

HRID 1348586 reaction equation
[NH2:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C@H:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:7](O)=[O:8].Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:14]([O:13][C:11](=[O:12])[NH:10][C@@H:6]1[C:7](=[O:8])[NH:1][C:2]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=2[O:4][CH2:5]1)([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67076752HCID 67076752, compound

Product 1

HCID 67076923HCID 67076923, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.96 g (6.24 mmol) (S)-3-(2-Amino-4-fluoro-phenoxy)-2-tert-butoxycarbonylamino-propionic acid and 1.20 g (6.24 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimid-hydrochloride in 25 ml dimethylformamide were stirred overnight at room temperature. Extraction with water/ethylacetate and removal of the solvent by distillation yielded 1.58 g (86%) ((S)-2-fluoro-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester, MS m/e (%): 314 (M+NH4+, 13), 297 (M+H+, 40), 241 (100), 197 (63).

Workup

  1. extractionExtraction
  2. customwith water/ethylacetate and removal of the solvent
  3. distillationby distillation

Sources & evidence

ORD record
ord-ef1fb9cbad5e4e398020ffea810d4cb6
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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