N-Carbobenzoxy-L-valine → HCID 18649007, compound

HRID 373764Notes

Reaction equation

HRID 373764 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[CH2:20]([O:22][C:23](=[O:35])[CH2:24][NH:25][CH:26]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27]1)[CH3:21].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:20]([O:22][C:23](=[O:35])[CH2:24][N:25]([C:16](=[O:18])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH:26]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27]1)[CH3:21]

Participants

6

Reactant 3

HCID 726987N-Carbobenzoxy-L-valineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13132277HCID 13132277, compound

Product 1

HCID 18649007HCID 18649007, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of CBZ-L-valine (5.0 g, 0.02 mol)in CH2Cl2 (50 mL) were added 4-dimethylaminopyridine (2.44 g, 0.02 mol), N-(2-indanyl)glycine ethyl ester hydrochloride (5.6 g, 0.02 mol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSCDI) (3.83 g, 0.02 mol). Approximately 20 mL CH2Cl2 was used to wash the reagents into the reaction flask. After the mixture was stirred overnight the solvent was removed under vacuo and the residue treated with ethyl acetate: 1N HCl (3:1). The separated organic layer was washed with 1N HCl, 5% aqueous Na2CO3 and saturated aqueous NaCl-solution followed by drying over magnesium sulfate and filtration. After removal of the solvent under reduced pressure an oil (4.3 g) remained, which was purified over silica gel using CH2Cl2 as eluent. 3.4 g of a colorless oil was collected (Rf: 0.7, silica gel, CH2Cl2 :CH2OH 97:3 ) and used as is for saponification.

Workup

  1. washto wash the reagents into the reaction flask
  2. customwas removed under vacuo
  3. additionthe residue treated with ethyl acetate
  4. washThe separated organic layer was washed with 1N HCl, 5% aqueous Na2CO3 and saturated aqueous NaCl-solution
  5. dry with materialby drying over magnesium sulfate and filtration
  6. customAfter removal of the solvent under reduced pressure an oil (4.3 g)
  7. customwhich was purified over silica gel
  8. custom3.4 g of a colorless oil was collected (Rf: 0.7, silica gel, CH2Cl2 :CH2OH 97:3 )

Sources & evidence

ORD record
ord-13f8b13639d443f6b409c615d0a3c355
Source dataset
uspto-grants-1992_11
Patent number
US05166154

Reaction notes

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