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

HRID 1588236Notes

Reaction equation

HRID 1588236 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 (5.1 g, 0.02 mol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSCDI), (3.83 g, 0.02 mol). Approximately 20 mL of CH2Cl2 was used to wash the reagents into the reaction flask. After the mixture was stirred over night the solvent was evaporated off and the residue was treated with ethyl acetate: HCl. 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. The titled product (3.4g) was collected as a colorless oil (Rf: 0.7,silica gel, CH2Cl2 : CH3OH 97:3 ) and used it as is for saponification.

Workup

  1. washto wash the reagents into the reaction flask
  2. customwas evaporated off
  3. additionthe residue was 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. customThe titled product (3.4g) was collected as a colorless oil (Rf: 0.7,silica gel, CH2Cl2 : CH3OH 97:3 )

Sources & evidence

ORD record
ord-558824b842e544948daf5bd505eae6a4
Source dataset
uspto-grants-1993_06
Patent number
US05221665

Reaction notes

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