Sodium Hydroxide → HCID 19091325, compound

HRID 487867Notes

Reaction equation

HRID 487867 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:31])[CH:7]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:21]=1)[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])C>C1COCC1>[CH2:12]([O:11][C:9]([NH:8][CH:7]([C:6]([OH:31])=[O:5])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:21]=1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19091322HCID 19091322, compound

Product 1

HCID 19091325HCID 19091325, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1N NaOH (107 mL) to the product of Step A (14.80 g) in THF (100 mL) and stir overnight. Concentrate the THF solution in vacuo and partition between EtOAc (700 mL)/2N HCl (200 mL). Concentrate the dried (MgSO4) EtOAc solution in vacuo to a residue. Add CH2Cl2 (50 mL) and concentrate in vacuo (3 times) to give N-benzyloxycarbonyl-3-methanesulfonamido-D,L-phenylalanine.

Workup

  1. concentrationConcentrate the THF solution in vacuo
  2. custompartition between EtOAc (700 mL)/2N HCl (200 mL)
  3. concentrationConcentrate the
  4. dry with materialdried (MgSO4) EtOAc solution in vacuo to a residue
  5. concentrationAdd CH2Cl2 (50 mL) and concentrate in vacuo (3 times)

Sources & evidence

ORD record
ord-6ef29506c8b346bfad1dcdec32b89d06
Source dataset
uspto-grants-1994_03
Patent number
US05298492

Reaction notes

Loading…