Diisopropylethylamine → Methyl 2-[(5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][(benzyloxy)(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentyl)oxy]-6-hydroxybenzoate

HRID 488662Notes

Reaction equation

HRID 488662 reaction equation
N[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:8]=1[C:9]([O:11][CH3:12])=[O:10].[C:18]([NH:21][C@H:22]([C:67]([OH:69])=O)[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]([C:53](=[O:64])[C:54]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[O:55])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([O:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])=[C:26]([CH2:65][CH3:66])[CH:25]=1)(=[O:20])[CH3:19].F[B-](F)(F)F.[N:75]1(OC(N(C)C)=[N+](C)C)[C:79]2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[C:18]([NH:21][CH:22]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]([C:53](=[O:64])[C:54]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[O:55])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([O:39][CH:40]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:38])=[C:26]([CH2:65][CH3:66])[CH:25]=1)[C:67]([NH:75][CH2:79][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:69])(=[O:20])[CH3:19]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11832643Methyl 2-(4-aminobutoxy)-6-hydroxybenzoateHCID 69803959N-acetyl-4-{2-[(benzhydryloxy)carbonyl][(benzyloxy)(oxo)acetyl]anilino}-3-ethylphenylalanine

Product 1

HCID 22271917Methyl 2-[(5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][(benzyloxy)(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentyl)oxy]-6-hydroxybenzoateYield 57.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-(4-aminobutoxy)-6-hydroxybenzoate (42 mg, 0.12 mmol), N-acetyl-4-{2-[(benzhydryloxy)carbonyl][(benzyloxy)(oxo)acetyl]anilino}-3-ethylphenylalanine (70 mg, 0.1 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (32 mg, 0.1 mmol) and diisopropylethylamine (70 μL, 0.4 mmol) in N,N-dimethylformamide (1 mL) was stirred at ambient temperature overnight, diluted with ethyl acetate and washed with aqueous NaHCO3 (1×30 mL), brine (2×30 mL), dried (MgSO4), filtered and concentrate under reduced pressure. The residue was purified on silica gel eluting with ethyl acetate to provide of titled compound 54 mg.

Workup

  1. washwashed with aqueous NaHCO3 (1×30 mL), brine (2×30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrate under reduced pressure
  5. customThe residue was purified on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-9b6992a029ca4c3eadb4348f818fcc09
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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