HCID 86607058, compound → HCID 86607057, compound

HRID 2252983Notes

Reaction equation

HRID 2252983 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH2:16][C:17](=[N:23][OH:24])[C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:9]1)(OC(C)(C)C)=O>C(O)(C(F)(F)F)=O>[OH:24][N:23]=[C:17]1[C:18]([O:21][CH3:22])=[CH:19][CH:20]=[C:15]([CH2:14][C@H:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH2:16]1

Participants

3

Reactant 1

HCID 86607058HCID 86607058, compound

Product 1

HCID 86607057HCID 86607057, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Intermediate (a) N-BOC-(R)-2-(3-hydroxyimino-4-methoxybenzyl)morpholine (85 mg, 0.24 mmol) was dissolved in TFA (20% v/v in dichloromethane, 5 mL total) and stirred at room temperature for 2 hrs. The reaction mixture was added directly to an SCX-2 column (1 g) and washed with dichloromethane (2 mL×2) and methanol (2 mL×2). The SCX-2 column was then washed with ammonia (2N in methanol, 3×2 mL). Combined ammonia washes were concentrated in vacuo to yield the crude product as a yellow solid (38 mg). The crude material was purified by HPLC to yield the desired morpholine example 25 as a white powder (12 mg).

Workup

  1. additionThe reaction mixture was added directly to an SCX-2 column (1 g)
  2. washwashed with dichloromethane (2 mL×2) and methanol (2 mL×2)
  3. washThe SCX-2 column was then washed with ammonia (2N in methanol, 3×2 mL)
  4. concentrationCombined ammonia washes were concentrated in vacuo
  5. customto yield the crude product as a yellow solid (38 mg)
  6. customThe crude material was purified by HPLC

Sources & evidence

ORD record
ord-cd5769cc3eb2447ba9bae4ece87a2741
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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