Hydroxylamine → HCID 75045532, compound

HRID 1926213Notes

Reaction equation

HRID 1926213 reaction equation
[CH:1]1[C:11]2[C:10]3[CH2:12][CH2:13][CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6](=[CH:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=O)=[O:18])[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(OCC)=O.[NH2:41][OH:42]>[Cl-].[Na+].O.CN(C=O)C>[CH:1]1[C:11]2[C:10]3[CH2:12][CH2:13][CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6](=[CH:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([NH:41][OH:42])=[O:27])=[O:18])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 67520808HCID 67520808, compound

Product 1

HCID 75045532HCID 75045532, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

6-(2-(10,11-dihydro-5H-dibenzocyclohepten-5-ylidene)acetamido)hexanoic acid (363 mg, 1 mmol), triethylamine (151 mg, 1.5 mmol) and 20 ml of DMF were stirred at 0° C. while ethyl chloroformate (163 mg, 1.5 mmol) was added. The mixture was stirred at 0° C. for 2 hours, and then 50% aqueous solution of hydroxylamine (1.32 g, 20 mmol) was added. The mixture was stirred for 3 hours at room temperature, and then diluted with 1000 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (178 mg, 47%) as a yellow solid. LC-MS (m/z) 379 (M+1).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 3 hours at room temperature
  3. filtrationThe solids were collected by vacuum filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1c9ee44325084ef5846948bb42ebc4a5
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

Loading…