Dicyclohexylcarbodiimide → HCID 67441681, compound

HRID 1253574Notes

Reaction equation

HRID 1253574 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]5[CH:29]=[CH:28][C:27]([CH2:30][N:31]6[CH2:36][CH2:35][N:34]([C:37](=[O:40])[CH2:38][OH:39])[CH2:33][CH2:32]6)=[CH:26][N:25]=5)[S:23][C:16]=34)=[C:10]([F:41])[CH:9]=2)=[O:6])[CH2:3][CH2:2]1.[C:42]([NH:49][C@H:50]([C:54](O)=[O:55])[CH:51]([CH3:53])[CH3:52])([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43].C1CCC(N=C=NC2CCCCC2)CC1.CO.C(Cl)Cl>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:45]([O:44][C:42]([NH:49][C@@H:50]([CH:51]([CH3:53])[CH3:52])[C:54]([O:39][CH2:38][C:37]([N:34]1[CH2:33][CH2:32][N:31]([CH2:30][C:27]2[CH:26]=[N:25][C:24]([C:22]3[S:23][C:16]4[C:17](=[N:18][CH:19]=[CH:20][C:15]=4[O:14][C:11]4[CH:12]=[CH:13][C:8]([NH:7][C:5]([NH:4][CH:1]5[CH2:2][CH2:3]5)=[O:6])=[CH:9][C:10]=4[F:41])[CH:21]=3)=[CH:29][CH:28]=2)[CH2:36][CH2:35]1)=[O:40])=[O:55])=[O:43])([CH3:48])([CH3:47])[CH3:46]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 83693Boc-L-ValineHCID 21226129Dichloromethane methanolHCID 53465337HCID 53465337, compound

Product 1

HCID 67441681HCID 67441681, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 74 (117 mg, 0.20 mmol), Boc-L-valine (132 mg, 0.61 mmol) and DMAP (25 mg, 0.20 mmol) in anhydrous DMF (4 ml) under nitrogen was added DCC reagent (251 mg, 1.22 mmol), and the reaction mixture was stirred at rt for 24 h. The reaction mixture was partitioned between AcOEt and a saturated aqueous solution of sodium bicarbonate. After separation, the organic layer was successively washed with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of ammonium chloride and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by Biotage (Snap 25 g cartridge; MeOH/DCM: 1/99 to 10/90 over 20 CV, then 10/90 over 5 CV), to afford the desired product 74-A (151 mg, 0.195 mmol, 96% yield) as a colorless-white sticky foam. MS (m/z): 776.7 (M+H).

Workup

  1. customThe reaction mixture was partitioned between AcOEt
  2. customAfter separation
  3. washthe organic layer was successively washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materiala saturated aqueous solution of ammonium chloride and brine, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by Biotage (Snap 25 g cartridge

Sources & evidence

ORD record
ord-ff71784b484f4b1cb3a9e24f58b1602f
Source dataset
uspto-grants-2013_06
Patent number
US08455484B2

Reaction notes

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