Hydroxylamine → HCID 178494954, compound

HRID 1893196Notes

Reaction equation

HRID 1893196 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([CH:9]([C:25]#[N:26])[CH2:10][CH2:11][C:12]([O:23][CH3:24])([CH3:22])[CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[NH2:28][OH:29]>CO>[Si:15]([O:14][CH2:13][C:12]([O:23][CH3:24])([CH3:22])[CH2:11][CH2:10][CH:9]([N:7]([CH3:8])[C:6](=[O:27])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:25]([NH:28][OH:29])=[NH:26])([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 59271881HCID 59271881, compound

Product 1

HCID 178494954HCID 178494954, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl(5-{[tert-butyl(dimethyl)silyl]oxy}-1-cyano-4-methoxy-4-methylpentyl)methylcarbamate (4.37 kg, 10.91 mol) in MeOH (28 L) at 30° C. was added aqueous hydroxylamine (50% in water, 1.2 L, 19.63 mol). The resulting mixture was heated to 40° C. overnight, then cooled and concentrated in vacuo. The crude residue was dissolved in 1.5 L of toluene, concentrated under reduced pressure, and dried in vacuo. The crude material was used in the next step without further purification. LC-MS: 434.3.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude residue was dissolved in 1.5 L of toluene
  4. concentrationconcentrated under reduced pressure
  5. customdried in vacuo
  6. customThe crude material was used in the next step without further purification

Sources & evidence

ORD record
ord-ad3502af8d76402582aca39ec4ea7376
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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