4-Nitrocatechol → (2S)-(-)-N-(7-Amino-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-sulfamide

HRID 533445Notes

Reaction equation

HRID 533445 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C@H:10]([CH2:13][NH:14][S:15]([NH2:18])(=[O:17])=[O:16])[O:9][C:8]=2[CH:19]=1)([O-])=O.[N+](C1C=C(O)C(=CC=1)O)([O-])=O>CO.Cl.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C@H:10]([CH2:13][NH:14][S:15]([NH2:18])(=[O:17])=[O:16])[O:9][C:8]=2[CH:19]=1

Participants

6

Reactant 2

HCID 35051094-NitrocatecholHCID 66687687(2S)-(-)-N-(2,3-Dihydro-7-nitro-benzo[1,4]dioxin-2-ylmethyl)-sulfamide2×

Product 1

HCID 17751570(2S)-(-)-N-(7-Amino-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-sulfamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

(2S)-(−)-N-(2,3-Dihydro-7-nitro-benzo[1,4]dioxin-2-ylmethyl)-sulfamide (1.2 g, 4.15 mmol), was prepared from 4-nitrocatechol according to the process outlined in Example 4. The (2S)-(−)-N-(2,3-Dihydro-7-nitro-benzo[1,4]dioxin-2-ylmethyl)-sulfamide, was then combined with 10% Pd/C in methanol (120 mL) and shaken under hydrogen atmosphere (39 psi) at room temperature for 3 h. The solids were filtered and washed with 10% M in DCM and the filtrate was evaporated in vacuo to yield crude product. The crude product was dissolved in 0.2 N HCl (25 mL), frozen and lyophilized to yield the title compound as a white flaky solid, as the corresponding hydrochloride salt.

Workup

  1. filtrationThe solids were filtered
  2. washwashed with 10% M in DCM
  3. customthe filtrate was evaporated in vacuo
  4. customto yield crude product
  5. temperaturefrozen

Sources & evidence

ORD record
ord-529ceb5b432d401bbced8f2d8b7ec0e0
Source dataset
uspto-grants-2014_10
Patent number
US08853263B2

Reaction notes

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