N-carbobenzyloxyalanine → HCID 67694773, compound

HRID 1457583Notes

Reaction equation

HRID 1457583 reaction equation
[CH:1]1([N:8]([C:25]2[CH:30]=[CH:29][C:28]([N:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=2)[C:9](=[O:24])[NH:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:12]=2[OH:23])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:34]([O:41][C:42]([NH:44][C@H:45]([C:47](O)=[O:48])[CH3:46])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:34]([O:41][C:42]([NH:44][C@H:45]([C:47]([O:23][C:12]1[C:13]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=1[NH:10][C:9]([N:8]([CH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:25]1[CH:30]=[CH:29][C:28]([N:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=1)=[O:24])=[O:48])[CH3:46])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 736104N-carbobenzyloxyalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10004070HCID 10004070, compound

Product 1

HCID 67694773HCID 67694773, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g of 2-[3-cycloheptyl-3-(4-dimethylaminophenyl)ureido]-4-methoxy-6-tert-butylphenol, 2.16 g of N-benzyloxycarbonyl-L-alanine, 1.95 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC), 0.62 g of 4-dimethylaminopyridine (DMPA) and 30 ml of dimethylformamide (DMF) was stirred at room temperature for 5 hours. A saturated saline solution was added to the mixture and the mixture was extracted with ethyl acetate. The extract was washed and dried. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1) to give 1.3 g of O-(N-benzyloxycarbonyl-L-alanyl)-2-[3-cycloheptyl-3-(4-dimethylaminophenyl)ureido]-4-methoxy-6-tert-butylphenol (yield: 60%, melting point: 126° C.).

Workup

  1. additionA saturated saline solution was added to the mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed
  4. customdried
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-7cd60b6ca7ba4ce4a744013759ed956a
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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