HCID 86601370, compound → HCID 59166817, compound

HRID 1443061Notes

Reaction equation

HRID 1443061 reaction equation
C([O:8][C:9]1[CH:29]=[CH:28][CH:27]=[CH:26][C:10]=1[O:11][CH2:12][C@H:13]1[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:29]=[CH:28][CH:27]=[CH:26][C:10]=1[O:11][CH2:12][C@H:13]1[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:14]1

Participants

4

Reactant 1

HCID 86601370HCID 86601370, compound

Product 1

HCID 59166817HCID 59166817, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Additional debenzylation reaction: To a solution of (S)-2-(2-benzyloxy-phenoxymethyl)-morpholine-4-carboxylic acid, tert-butyl ester (obtained as above, General Procedure D) in ethanol was treated with 10% Pd/C. The room temperature sample was hydrogenated at balloon pressure for 2 h, filtered then concentrated. The sample was dissolved into EtOAc, washed with sat. KH2PO4 and brine solutions, dried (MgSO4), filtered and concentrated to give (S)-2-(2-hydroxy-phenoxymethyl)-morpholine-4-carboxylic acid, tert-butyl ester as a light yellow oil.

Workup

  1. customAdditional debenzylation reaction
  2. filtrationfiltered
  3. concentrationthen concentrated
  4. dissolutionThe sample was dissolved into EtOAc
  5. washwashed with sat. KH2PO4 and brine solutions
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-45d5d34dd92c40a181c9e7fd47add33a
Source dataset
uspto-grants-2010_02
Patent number
US07659394B2

Reaction notes

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