Dimethylformamide → HCID 19757311, compound

HRID 1588089Notes

Reaction equation

HRID 1588089 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:5][CH:4]=1)#[N:2].CN(C)C=O.C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)C(=O)C1.[CH:39]1[CH:44]=[CH:43][C:42]([CH:45]([NH2:50])[CH2:46][C:47]([OH:49])=[O:48])=[CH:41][CH:40]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:50][CH:45]([C:42]2[CH:43]=[CH:44][CH:39]=[CH:40][CH:41]=2)[CH2:46][C:47]([OH:49])=[O:48])=[O:15])=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 69189DL-beta-PhenylalanineHCID 676246Di(succinimido) carbonateHCID 152807295-(4-Cyanophenyl)pentanoic acid

Product 1

HCID 19757311HCID 19757311, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 5-(p-cyanophenyl)pentanoic acid (1.00g, 4.93 mmol), dimethylformamide (10 mL), and pyridine (2 mL) was added N,N'-disuccinimidylcarbonate (1.24 g, 4.85 mmol) and 4-dimethylaminopyridine (60 mg, 0.493 mmol) under an argon atmosphere at 23° C. After 5 h, DL-3-amino-3-phenylpropionic acid (0.814 g, 4.93 mmol) was added as a solid, followed immediately by N,N'-diisopropylethyl amine (0.627 g, 4.85 mmol). After 20 h at 23° C., the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (300 mL), washed with KHSO4 (2×50 mL), washed with brine (1×50 mL), dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography (2 liters ethyl acetate: chloroform:acetic acid 50:50:0.5 followed by 2 liters of ethyl acetate:methanol:acetic acid 89:10:1) to afford 850 mg (50%) of the title compound (compound 6 of Scheme D). The product was verified by C NMR (CDCl3) delta 24.9, 29.9, 35.3, 35.7, 40.5, 49.7, 109.1, 118.9, 126.1, 127.4, 128.5, 129.0, 131.9, 140.5, 147.8, 173.4, 176.4.

Workup

  1. waitAfter 20 h at 23° C.
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  4. washwashed with KHSO4 (2×50 mL)
  5. washwashed with brine (1×50 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (2 liters ethyl acetate: chloroform:acetic acid 50:50:0.5 followed by 2 liters of ethyl acetate:methanol:acetic acid 89:10:1)

Sources & evidence

ORD record
ord-f3388e37d0d64d53bfd58fe3e37c4953
Source dataset
uspto-grants-1993_06
Patent number
US05220050

Reaction notes

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