tert-butyl N-(4-aminobutyl)carbamate → N'-(tert-butoxycarbonyl)-N-(2-naphthyl-acetyl)-1,4-diamino-butane

HRID 973731Notes

Reaction equation

HRID 973731 reaction equation
[C:1]1(OCC(Cl)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:16]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][NH2:28])=[O:22])([CH3:19])([CH3:18])[CH3:17].[O:29]1CC[CH2:31][CH2:30]1>C(N(CC)CC)C>[C:16]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:30](=[O:29])[CH2:31][C:3]1[CH:2]=[CH:1][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 8028Tetrahydrofuran2×HCID 292530(1-Naphthyloxy)acetyl chloride

Product 1

HCID 19989025N'-(tert-butoxycarbonyl)-N-(2-naphthyl-acetyl)-1,4-diamino-butane

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

11.16 g of naphthoxy acetic acid chloride in solution in 50 ml of tetrahydrofuran were added at 0° C. to +10° C. to a solution of 10.32 g of N-(tert-butoxycarbonyl)-1,4-diamino butane in 110 ml of tetrahydrofuran and 6.7 g of triethylamine. The mixture was stirred for 90 minutes at ambient temperature and the insoluble part was filtered off. The fitrate was evaporated to dryness and the 17.78 g of residue were chromatographed on silica (eluant: hexane-ethyl acetate (1-1)) to obtain 10 g of the expected product melting at 102° C.

Workup

  1. filtrationthe insoluble part was filtered off
  2. customThe fitrate was evaporated to dryness
  3. customthe 17.78 g of residue were chromatographed on silica (eluant: hexane-ethyl acetate (1-1))

Sources & evidence

ORD record
ord-f795ab52c1574e50b8c8a637f6800bc3
Source dataset
uspto-grants-1991_11
Patent number
US05064861

Reaction notes

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