Ammonium Chloride → HCID 57798963, compound

HRID 2100365Notes

Reaction equation

HRID 2100365 reaction equation
[CH2:1]([O:8][P:9]([O:19][CH2:20][O:21][C:22](=[O:39])[N:23]([CH:36]1[CH2:38][CH2:37]1)[C:24](=[O:35])[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([N+:32]([O-])=O)[CH:26]=1)([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>CO.C1COCC1.[Zn]>[CH2:12]([O:11][P:9]([O:19][CH2:20][O:21][C:22](=[O:39])[N:23]([C:24](=[O:35])[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([NH2:32])[CH:26]=1)[CH:36]1[CH2:38][CH2:37]1)([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 57799004HCID 57799004, compound

Product 1

HCID 57798963HCID 57798963, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (bis(benzyloxy)phosphoryloxy)methyl-cyclopropyl(4-methyl-3-nitrobenzoyl)carbamate (0.53 g, 1.0 mmol) in MeOH/THF (1:1, 50 mL) under nitrogen were added ammonium chloride (0.79 g, 14.8 mmol) and zinc (0.75 g, 11.5 mmol). After 3 h, the precipitate was filtered, and the filtrate was concentrated in vacuo, diluted with EtOAc and washed with water (2×), brine successively, dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound as a colorless oil (0.51 g, 100% yield). (M+H)+=525.19.

Workup

  1. filtrationthe precipitate was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. additiondiluted with EtOAc
  4. washwashed with water (2×), brine successively
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f74d4c3cb85941f993d067307f64066f
Source dataset
uspto-grants-2009_08
Patent number
US07572795B2

Reaction notes

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