N-benzyloxycarbonyl-l-tyrosine → HCID 10650932, compound

HRID 1078616Notes

Reaction equation

HRID 1078616 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:9]1=[O:19])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([O:28][C:29]([NH:31][C@H:32]([C:41](O)=[O:42])[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:41](=[O:42])[C@H:32]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=2)[NH:31][C:29]([O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:30])[C@@H:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:9]1=[O:19])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 712438N-benzyloxycarbonyl-l-tyrosineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10636945HCID 10636945, compound

Product 1

HCID 10650932HCID 10650932, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 15 ml of dichloromethane were dissolved 1.65 g of (S)-3-methoxycarbonylmethyl-2-oxopiperazine-1-acetic acid tert-butyl ester and 1.9 g of N-benzyloxycarbonyl-L-tyrosine. To the solution was added, while stirring for one hour, 1.44 g of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, and the mixture was stirred for one hour. The reaction mixture was concentrated under reduced pressure to leave an oily substance, which was dissolved in ethyl acetate. The organic layer was washed with a 5% aqueous solution of potassium hydrogen carbonate and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was subjected to a silica gel column chromatography (eluent: ethyl acetate: hexane=7:3) to afford 2.0 g of (S)-4-(N-benzyloxycarbonyl-L-tyrosyl)-3-methoxycarbonylmethyl-2-oxopiperazine-1-acetic acid tert-butyl ester as a colorless oily product. IR γmax cm-1 : 3332, 2952, 1740, 1646, 1613, 1514, 1444, 1367, 1227, 1153. NMR(CDCl3) δ: 1.46(9H,s), 2.30-2.53(1H,m), 2.72-3.13(5H,m), 3.50-3.72(2H,m), 3.63(3H,s), 3.85(1H,d,J=12 Hz), 4.07(1H,d,J=12 Hz), 4.70-4.90(1H,m), 4.90-5.05(1H,m), 5.11(2H,s), 5.50-5.67(2H,m), 6.76(2H,d,J=8.2 Hz), 7.03(2H,d,J=8.2 Hz), 7.36(5H,s).

Workup

  1. additionTo the solution was added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto leave an oily substance, which
  4. washThe organic layer was washed with a 5% aqueous solution of potassium hydrogen carbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-efc0f116965d463eaff21ad067033b68
Source dataset
uspto-grants-1996_08
Patent number
US05550131

Reaction notes

Loading…