Benzyl chloroformate → diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate

HRID 2230403Notes

Reaction equation

HRID 2230403 reaction equation
Cl.[OH:2][C@@H:3]([C@H:18]([OH:33])[C@H:19]([OH:32])[C@@H:20]([NH:23][C:24](=[O:31])[C@H:25]([CH2:27][CH:28]([CH3:30])[CH3:29])[NH2:26])[CH2:21][OH:22])[C:4]([NH:6][C@H:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8][C:9]([OH:11])=[O:10])=[O:5].[C:34]1([C:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[N+]=[N-])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])O.[Na+].Cl[C:55]([O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:56]>CO.O>[CH2:58]([O:57][C:55]([NH:26][C@H:25]([C:24]([NH:23][C@@H:20]([CH2:21][OH:22])[C@@H:19]([OH:32])[C@@H:18]([OH:33])[C@H:3]([OH:2])[C:4]([NH:6][C@H:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:8][C:9]([O:11][CH:40]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:10])=[O:5])=[O:31])[CH2:27][CH:28]([CH3:29])[CH3:30])=[O:56])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1

Participants

7

Reactant 4

HCID 10387Benzyl chloroformateHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 516892Sodium BicarbonateHCID 69823761(S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid hydrochloride

Product 1

HCID 59902693diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid hydrochloride (4.35 g) in methanol (100 ml) was added a solution of diphenyldiazomethane (3.40 g) in methanol (100 ml) under ice-cooling and the mixture was stirred at room temperature for 15 hours. Removal of the organic solvent gave a residue, which was suspended in water (200 ml). To the suspension were added sodium hydrogencarbonate (2.20 g) and benzyl chloroformate (18 ml) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with ethyl acetate and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (5.95 g).

Workup

  1. temperaturecooling
  2. customRemoval of the organic solvent
  3. customgave a residue, which
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washthe extract was washed with saturated brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-60b024f9d5514479995a54a6382c7a32
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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