O-(Tetrahydropyran-2-yl)hydroxylamine → HCID 88066573, compound

HRID 1978091Notes

Reaction equation

HRID 1978091 reaction equation
C[Al](C)C.[O:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:11][NH2:12].[CH2:13]([O:20][C@H:21]([C:39](OC)=[O:40])[C@@H:22]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:23]([NH:25][N:26]([CH2:31][CH:32]([CH3:34])[CH3:33])[S:27]([CH3:30])(=[O:29])=[O:28])=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:13]([O:20][C@H:21]([C:39](=[O:40])[NH:12][O:11][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][O:5]1)[C@@H:22]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:23]([NH:25][N:26]([CH2:31][CH:32]([CH3:33])[CH3:34])[S:27]([CH3:30])(=[O:28])=[O:29])=[O:24])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 16682925TrimethylaluminumHCID 69944175HCID 69944175, compound

Product 1

HCID 88066573HCID 88066573, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

0.530 ml of a 2M solution of trimethylaluminium in toluene was added to a solution of 0.124 g of O-(tetrahydro-2H-pyran-2(RS)-yl)-hydroxylamine in 5 ml of dry toluene at 0° C. under a nitrogen atmosphere. The mixture was stirred at 0° C. for 0.5 hours and then 0.335 g of 2(R)-[(S)-(benzyloxy)(methoxycarbonyl)methyl]-2′-isobutyl-2′-(methanesulphonyl)-4-methylvalerohydrazide was added in one portion. The mixture was then left to warm to room temperature overnight. The mixture was diluted with ethyl acetate and washed in succession with 2M aqueous hydrochloric acid and 5% aqueous sodium hydrogen carbonate solution and then dried over anhydrous magnesium sulphate. The solvent was evaporated and the residue was triturated with hexane/diethyl ether (2:1) to give 0.119 g of 2(R)-[(S)-(benzyloxy)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]methyl]-2′-isobutyl-2′-(methanesulphonyl)-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. waitThe mixture was then left
  2. temperatureto warm to room temperature overnight
  3. washwashed in succession with 2M aqueous hydrochloric acid and 5% aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customThe solvent was evaporated
  6. customthe residue was triturated with hexane/diethyl ether (2:1)

Sources & evidence

ORD record
ord-10d2861b64f94e1c8792e6d9220da452
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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