N-[(2-methoxyphenyl)methylidene]hydroxylamine → Tert-butyl 2-(3-methoxycarbonyladamant-1-ylcarbonylamino)-3-[3-(2-methoxyphenyl)isoxazol-5-yl]propionate

HRID 991765Notes

Reaction equation

HRID 991765 reaction equation
[O-]Cl.[Na+].[CH3:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[CH:8]=[N:9][OH:10].[CH3:15][O:16][C:17]([C:19]12[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][C:21]([C:29]([NH:31][CH:32]([CH2:40][C:41]#[CH:42])[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:30])([CH2:22]3)[CH2:20]1)[CH2:26]2)=[O:18]>C(Cl)(Cl)Cl.CCN(CC)CC>[CH3:15][O:16][C:17]([C:19]12[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][C:21]([C:29]([NH:31][CH:32]([CH2:40][C:41]4[O:10][N:9]=[C:8]([C:7]5[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=5[O:5][CH3:4])[CH:42]=4)[C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])=[O:30])([CH2:22]3)[CH2:20]1)[CH2:26]2)=[O:18]

Participants

6

Reactant 3

HCID 141489N-[(2-methoxyphenyl)methylidene]hydroxylamineHCID 21940505tert-Butyl 2-(3-methoxycarbonyladamant-1-ylcarbonylamino)pent-4-ynoateHCID 23665760Sodium Hypochlorite

Product 1

HCID 21940557Tert-butyl 2-(3-methoxycarbonyladamant-1-ylcarbonylamino)-3-[3-(2-methoxyphenyl)isoxazol-5-yl]propionate

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 5.25% aqueous NaOCl (1.33 g, 0.77 mmol) in CHCl3 at 0° C. was added a solution of 2-methoxybenzaldehyde oxime (0.77 mmol, 0.116 g) dropwise and tert-butyl 2-(3-methoxycarbonyladamant-1-ylcarbonylamino)pent4-ynoate (300 mg, 0.77 mmol) and one drop of Et3N. After addition, the reaction mixture was allowed to warm up to room temperature and stirred overnight. The solvent was evaporated under reduced pressure and the crude product was purified on a prep plate (silica gel; EtOAc/hexanes, 2:3) to afford the title compound.

Workup

  1. additionAfter addition
  2. customThe solvent was evaporated under reduced pressure
  3. customthe crude product was purified on a prep plate (silica gel; EtOAc/hexanes, 2:3)

Sources & evidence

ORD record
ord-da18913b9aab41a69375814acf5e958f
Source dataset
uspto-grants-2002_10
Patent number
US06465513B1

Reaction notes

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