Dimethylformamide → HCID 131736533, compound

HRID 1478980Notes

Reaction equation

HRID 1478980 reaction equation
[C:1]([NH:18][CH2:19][C:20]([OH:22])=O)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[CH:23]1(N=C=NC2CCCCC2)CC[CH2:26][CH2:25][CH2:24]1.[OH2:38].ON1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2N=N1.CO[C:51]1[CH:85]=[CH:84][C:54]([C:55]([O:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81]CN)(C2C=CC=CC=2)[C:56]2[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=2)=[CH:53][CH:52]=1.C[N:87]([CH3:90])[CH:88]=[O:89]>>[C:1]([NH:18][CH2:19][C:20]([NH:87][CH2:90][C:71]([OH:70])=[O:38])=[O:22])([O:3][CH2:4][CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:2].[CH3:1][O:2][CH:77]([CH2:78][CH2:79][CH2:80][CH2:81][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:76][CH:75]([CH2:74][CH2:73][CH2:72][CH2:71][O:70][C:55]([C:54]1[CH:84]=[CH:85][CH:51]=[CH:52][CH:53]=1)([C:56]1[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:88]([NH2:87])=[O:89]

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 10868DicyclohexylcarbodiimideHCID 93124Fmoc-Gly-OHHCID 27960291-Hydroxybenzotriazole hydrateHCID 117677742HCID 117677742, compound

Product 1

HCID 131736533HCID 131736533, compound

Procedure

To a solution (70 ml) of Fmoc-glycine (Fmoc-Gly-OH, purchased from Wako Pure Chemical Industries, Ltd.) (2.00 g, 6.73 mmol), dicyclohexylcarbodiimide (1.66 g, 8.07 mmol) and 1-hydroxybenzotriazole monohydrate (2.31 g, 16.14 mmol) in anhydrous N,N-dimethylformamide was added a solution (30 ml) of compound 2 (4.07 g, 8.07 mmol) in anhydrous N,N-dimethylformamide under an argon atmosphere at room temperature, and the mixture was stirred under an argon atmosphere at room temperature overnight. The resulting precipitate was filtered off, and the filtrate was concentrated under reduced pressure at 35° C. To the obtained residue was added dichloromethane (200 ml), and the mixture was washed 3 times with saturated aqueous sodium hydrogen carbonate. The organic layer was fractionated, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: dichloromethane-methanol (95:5)+0.05% pyridine) to give Fmoc-glycylglycine-4,4′-dimethoxytrityloxybutyldodecanamide (3) (5.88 g, q.) as a colorless syrup.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure at 35° C
  3. additionTo the obtained residue was added dichloromethane (200 ml)
  4. washthe mixture was washed 3 times with saturated aqueous sodium hydrogen carbonate
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent: dichloromethane-methanol (95:5)+0.05% pyridine)

Sources & evidence

ORD record
ord-a9be696f3da74169bbd9cbd83e51d65d
Source dataset
uspto-grants-2016_08
Patent number
US09404108B2

Reaction notes

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