L-(+)-Cysteine → HCID 54452303, compound

HRID 487868Notes

Reaction equation

HRID 487868 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:25]([OH:27])=[O:26])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C@H:29](C(O)=O)[CH2:30]S.C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O>CCO>[CH2:29]([O:26][C:25](=[O:27])[C@H:12]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:15]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH3:30]

Participants

5

Reactant 3

HCID 5862L-(+)-Cysteine3×HCID 31348Citrate3×HCID 19091325HCID 19091325, compound

Product 1

HCID 54452303HCID 54452303, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Treat the product of Step B (12.5 g) in EtOH (400 mL) with papain (2.56 g freshly ground), L-cysteine (0.156 g) and freshly made 1M citrate buffer pH 4.5 (2.8 mL). After 2 hr, add papain (1.28 g), L-cysteine (0.078 g), and 1M citrate buffer pH 4.5 (1.4 mL). Repeat the latter addition of papain, L-cystein, and citrate buffer at 4 and 6 hr intervals. Stir the resulting mixture for 4 days. Filter, wash with EtOH, and concentrate in vacuo to a residue. Partition the residue between Et2O (1400 mL)/5% NaHCO3 (6×150 mL). Concentrate the dried (MgSO4) Et2O solution in vacuo to give N-benzyloxycarbonyl-3-methanesulfonamido-L-phenylalanine ethyl ester, [α]26D =-6.7° (MeOH).

Workup

  1. filtrationFilter
  2. washwash with EtOH
  3. concentrationconcentrate in vacuo to a residue
  4. customPartition the residue between Et2O (1400 mL)/5% NaHCO3 (6×150 mL)
  5. concentrationConcentrate the
  6. dry with materialdried (MgSO4) Et2O solution in vacuo

Sources & evidence

ORD record
ord-8e111791709b467ab7d1240d9f803249
Source dataset
uspto-grants-1994_03
Patent number
US05298492

Reaction notes

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