L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → benzyl 3-(N-tertiarybutoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanoate

HRID 1872808Notes

Reaction equation

HRID 1872808 reaction equation
[OH:1][CH:2]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[C:28]([O:32][C:33]([NH:35][C@H:36]([C:44](O)=[O:45])[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:34])([CH3:31])([CH3:30])[CH3:29].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>ClCCl.CN(C)C1C=CN=CC=1>[C:28]([O:32][C:33]([NH:35][C@H:36]([C:44]([O:1][CH:2]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])=[O:45])[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:34])([CH3:30])([CH3:31])[CH3:29]

Participants

6

Reactant 3

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 18687221Benzyl 3-hydroxy-15-methylhexadecanoate

Product 1

HCID 21970290benzyl 3-(N-tertiarybutoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 3-hydroxy-15-methylhexadecanoate (1.77 g) and N-tertiarybutoxycarbonyl-L-phenylalanine (1.25 g) in dichloromethane (50 ml) was added benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (2.08 g) and 4-dimethylaminopyridine (1.22 g). The mixture was stirred at room temperature for 14 hours and evaporated. The residue 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 to give almost pure benzyl 3-(N-tertiary butoxycarbonyl-L-phenylalanyl)oxy-15-methylhexadecanoate, which can be used for next step without further purification (2.87 g).

Workup

  1. customevaporated
  2. additionThe residue was poured into a mixture of ethyl acetate and diluted hydrochloric acid
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9b28572beec845a383f1008956003a2c
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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