Hydroxylamine → HCID 178465443, compound

HRID 1893207Notes

Reaction equation

HRID 1893207 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([CH:10]([C:25]#[N:26])[CH2:11][CH2:12][C@H:13]([O:23][CH3:24])[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].[NH2:28][OH:29]>CCO>[C:1]([O:5][C:6](=[O:27])[N:7]([CH:10]([C:25]([NH:28][OH:29])=[NH:26])[CH2:11][CH2:12][C@H:13]([O:23][CH3:24])[CH2:14][O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:8][CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 59271815HCID 59271815, compound

Product 1

HCID 178465443HCID 178465443, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl[(4S)-5-(benzyloxy)-1-cyano-4-methoxypentyl]ethylcarbamate (74 g, 197 mmol) in EtOH (1000 mL) was added TEA (54.8 mL, 393 mmol) and NH2OH (50% in water, 14.45 mL, 236 mmol). The resulting solution was stirred at 40° C. overnight and then concentrated in vacuo. The residue was dissolved in MeOH and the solvent was removed under reduced pressure (3×) to remove water. The crude residue was used in the next reaction without further purification. LC-MS: 410.5 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in MeOH
  3. customthe solvent was removed under reduced pressure (3×)
  4. customto remove water
  5. customThe crude residue was used in the next reaction without further purification

Sources & evidence

ORD record
ord-e3881b1c9d3a4c29ab5fa83ecf785dcc
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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