Ammonia → 3-(N-tertiarybutoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanamide

HRID 1872810Notes

Reaction equation

HRID 1872810 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([O:19][CH:20]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH2:21][C:22](O)=[O:23])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:40]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.N.Cl>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([O:19][CH:20]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH2:21][C:22]([NH2:40])=[O:23])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219702703-(N-tertiarybutoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanoic acid

Product 1

HCID 219702693-(N-tertiarybutoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(N-tertiarybutoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanoic acid (2.30 g) in tetrahydrofuran (30 ml) was added 1-hydroxybenzotriazole (0.58 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.82 g). The mixture was stirred at room temperature for 30 minutes. 28% Ammonia solution (0.5 ml) was added to the mixture and then the mixture was stirred at room temperature for 2 hours. The mixture was poured into a mixture of ethyl acetate and diluted hydrochloric acid. The organic layer was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on a silica gel column eluting with chloroform to give 3-(N-tertiarybutoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanamide as white wax (1.41 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on a silica gel column
  6. washeluting with chloroform

Sources & evidence

ORD record
ord-bada4322f0c0492f8c46864994fdd025
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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