Sulfamide → HCID 53628413, compound

HRID 1025009Notes

Reaction equation

HRID 1025009 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:3]1.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.[S:30](N)([NH2:33])(=[O:32])=[O:31]>O1CCOCC1>[NH2:33][S:30]([N:2]1[CH2:5][CH:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:3]1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 82267SulfamideHCID 88675Proton spongeHCID 22101213tert-Butyl azetidin-3-ylcarbamate--hydrogen chloride (1/1)

Product 1

HCID 53628413HCID 53628413, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl azetidin-3-ylcarbamate hydrochloride (prepared according to J. Antibiot. 1986, 39, 1243-1256, 0.755 g), Proton-Sponge® (0.85 g) and sulfamide (0.42 g) in dioxane (23 ml) was heated at reflux for 48 h. The residue was partitioned between H2O and EtOAc, and the aqueous layer then extracted with further EtOAc (×4). The combined organic extracts were washed quickly with 2M aqueous hydrochloric acid (×3) then with saturated aqueous sodium bicarbonate, H2O and saturated aqueous sodium chloride, dried with sodium sulfate, filtered and evaporated to afford the subtitle compound as a pale brown powder. Yield: 0.44 g

Workup

  1. temperatureat reflux for 48 h
  2. customThe residue was partitioned between H2O and EtOAc
  3. extractionthe aqueous layer then extracted with further EtOAc (×4)
  4. washThe combined organic extracts were washed quickly with 2M aqueous hydrochloric acid (×3)
  5. dry with materialwith saturated aqueous sodium bicarbonate, H2O and saturated aqueous sodium chloride, dried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-705ac7f0ffd44f87b2f684e4372d9cc1
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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