Hydroxylamine → HCID 178501507, compound

HRID 1937819Notes

Reaction equation

HRID 1937819 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C@@H:4]([NH:11][C:12](=[O:33])[CH:13]([C:23](=[O:32])[NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[NH2:35][OH:36]>C(O)C>[CH3:1][O:2][C:3](=[O:34])[C@@H:4]([NH:11][C:12](=[O:33])[CH:13]([C:23](=[O:32])[NH:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21](=[NH:22])[NH:35][OH:36])=[CH:19][CH:20]=1)[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 131723233HCID 131723233, compound

Product 1

HCID 178501507HCID 178501507, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [2-(R,S)-benzylcarbamoyl-3-(4-cyano-phenyl)-propionylamino]-(S)-cyclohexyl-acetic acid methyl ester (9 g, 19.5 mmol) and hydroxylamine (3.22 g, 97.5 mmol) in ethanol (180 ml) was heated to reflux for 4 hours. The reaction mixture was cooled to room temperature, evaporated in vacuo, solved in ethanol and poured in ice-water. The precipitate was collected by suction and dried at 50° C. in vacuo to give 7.9 g (82%) of the desired product. mp.: 101-104° C., MS m/z: 495 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. customevaporated in vacuo
  4. additionpoured in ice-water
  5. customThe precipitate was collected by suction
  6. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-889859ab05a1442cb6a4e81be0e105d4
Source dataset
uspto-grants-2002_05
Patent number
US06395737B1

Reaction notes

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