O-Benzyl-N-[(benzyloxy)carbonyl]-L-threonine → HCID 18639971, compound

HRID 2165231Notes

Reaction equation

HRID 2165231 reaction equation
[CH2:1]([O:8][C@H:9]([CH3:25])[C@@H:10]([C:22]([OH:24])=[O:23])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:26][C:27]([F:46])([F:45])[C:28]([NH:30][C@H:31]([C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[CH2:32][CH2:33]O)=[O:29]>C(Cl)Cl>[CH2:1]([O:8][C@H:9]([CH3:25])[C@@H:10]([C:22]([O:24][CH2:33][CH2:32][C@@H:31]([C:35]([O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:36])[NH:30][C:28](=[O:29])[C:27]([F:46])([F:26])[F:45])=[O:23])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7018810O-Benzyl-N-[(benzyloxy)carbonyl]-L-threonineHCID 18639965HCID 18639965, compound

Product 1

HCID 18639971HCID 18639971, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of O-benzyl-N-benzyloxycarbonyl-L-threonine (1.5 g), benzyl N-trifluoroacetyl-L-homoserinate (1.34 g) and 4-N,N-dimethylaminopyridine (48.8 mg) in methylene chloride (30 ml) was added N,N-diethylaminopropyl-N'-ethylcarbodiimide hydrochloride (840 mg) at 0° C. After stirring for an hour at room temperature, the reaction mixture was concentrated. The residue was dissolved in ethyl acetate and washed successively with 0.1N hydrochloric acid, water, 10% aqueous sodium hydrogen carbonate, water and brine. After drying over sodium sulfate, the ethyl acetate extract was filtered and concentrated. The residue was chromatographed on silica gel eluting successively with a 1:1 mixture of methylene chloride and hexane, methylene chloride and a 50:1 mixture of methylene chloride and acetone (50:1) to give benzyl O-(O-benzyl-N-benzyloxycarbonyl-L-threonyl)-N-trifluoroacetyl-L-homoserinate (1.6 g).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed successively with 0.1N hydrochloric acid, water, 10% aqueous sodium hydrogen carbonate, water and brine
  4. dry with materialAfter drying over sodium sulfate
  5. extractionthe ethyl acetate extract
  6. filtrationwas filtered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting successively with a 1:1 mixture of methylene chloride and hexane, methylene chloride
  9. additiona 50:1 mixture of methylene chloride and acetone (50:1)

Sources & evidence

ORD record
ord-517fa4af55834c2bbcb02590f83d3086
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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