2-Naphthol → HCID 13188829, compound

HRID 1732974Notes

Reaction equation

HRID 1732974 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([O:20][C:21]([NH:23][C@H:24]([C:32]([OH:34])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17].[CH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][C:36]=1O>O1CCCC1>[CH:43]1[C:44]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:40]=[CH:41][C:42]=1[O:33][C:32](=[O:34])[C@H:24]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:23][C:21]([O:20][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:22]

Participants

5

Reactant 3

HCID 86632-NaphtholHCID 10868DicyclohexylcarbodiimideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 13188829HCID 13188829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.2 g of dicyclohexylcarbodiimide are added to a solution of 7.8 g of tert.-butyoxycarbonyl-L-phenylalanine and 5.3 g of β-naphthol in 50 ml of absolute tetrahydrofurane at 0° C. and the reaction mixture was kept at 4° C. for 12 hours. The dicyclohexylurea which had precipitated was then separated off by filtration and the filtrate was evaporated to dryness in vacuo. The crystalline residue was recrystallised twice from ethyl acetate/cyclohexane and finally from acetonitrile. 8.5 g (73% of theory) of melting point 118°-119° C. were obtained.

Workup

  1. customThe dicyclohexylurea which had precipitated
  2. customwas then separated off by filtration
  3. customthe filtrate was evaporated to dryness in vacuo
  4. customThe crystalline residue was recrystallised twice from ethyl acetate/cyclohexane and finally from acetonitrile
  5. custom8.5 g (73% of theory) of melting point 118°-119° C. were obtained

Sources & evidence

ORD record
ord-19f3b825e0dd496b98c9e5f8d7860e5d
Source dataset
uspto-grants-1980_12
Patent number
US04239902

Reaction notes

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