Hydrochloric Acid → 1-Benzyloxy-5-(benzyloxycarbonyl)-2-chloro-3-oxo-4-azapentane

HRID 399370

Reaction equation

HRID 399370 reaction equation
[Cl:1][CH:2]([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3](Cl)=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:26]([O:33][C:34](=[O:37])[CH2:35][NH2:36])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C.Cl>C(Cl)Cl.O>[CH2:8]([O:7][CH2:6][CH:2]([Cl:1])[C:3](=[O:4])[NH:36][CH2:35][C:34]([O:33][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:37])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 187637642-Chloro-3-(phenylmethoxy)propanoyl chloride

Product 1

HCID 225614381-Benzyloxy-5-(benzyloxycarbonyl)-2-chloro-3-oxo-4-azapentane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

76 g (326.1 mmol) of 2-chloro-3-(benzyloxy)-propionic acid chloride (produced according to Inorg. Chem. Vol. 31; 2422, 1992) is added in drops to 100 g (296.4 mmol) of glycine benzyl ester-p-toluenesulfonic acid salt and 33.0 g (326.1 mmol) of triethylamine in 400 ml of methylene chloride at 0° C., and it is stirred for 2 hours at this temperature. 500 ml of ice water is added, and the water phase is set at pH 2 with 10% aqueous hydrochloric acid. The organic phase is separated, washed once each with 300 ml of 5% aqueous hydrochloric acid, 300 ml of 5% aqueous soda solution and 400 ml of water. The organic phase is dried on magnesium sulfate and evaporated to dryness in a vacuum. The residue is chromatographed on silica gel (mobile solvent: methylene chloride/hexane/acetone=15/5/1).

Workup

  1. customThe organic phase is separated
  2. washwashed once each with 300 ml of 5% aqueous hydrochloric acid, 300 ml of 5% aqueous soda solution and 400 ml of water
  3. customThe organic phase is dried on magnesium sulfate
  4. customevaporated to dryness in a vacuum
  5. customThe residue is chromatographed on silica gel (mobile solvent: methylene chloride/hexane/acetone=15/5/1)

Sources & evidence

ORD record
ord-722192b16c664f5aafcdc3cfdb065602
Source dataset
uspto-grants-1998_10
Patent number
US05820849

Linked notes

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