Dicyclohexylcarbodiimide → HCID 86711156, compound

HRID 1055263Notes

Reaction equation

HRID 1055263 reaction equation
[CH3:1][C:2]1[N:12]=[C:11]2[N:6]([CH2:7][CH2:8][CH2:9][CH:10]2[OH:13])[C:4](=[O:5])[C:3]=1[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([C:22]2[C:23]3[CH:24]=[CH:25][C:26]([F:31])=[CH:27][C:28]=3[O:29][N:30]=2)[CH2:18][CH2:17]1.[NH:32]([C:38]([O:40]C(C)(C)C)=O)[CH2:33][CH2:34][C:35]([OH:37])=O.C1(N=C=N[CH:54]2[CH2:59][CH2:58]CCC2)CCCCC1.[C:60](=O)(O)[O-].[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[C:38]([NH:32][CH2:33][CH2:34][C:35]([O:13][CH:10]1[C:11]2=[N:12][C:2]([CH3:1])=[C:3]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH:19]([C:22]4[C:23]5[CH:24]=[CH:25][C:26]([F:31])=[CH:27][C:28]=5[O:29][N:30]=4)[CH2:18][CH2:17]3)[C:4](=[O:5])[N:6]2[CH2:7][CH2:8][CH2:9]1)=[O:37])(=[O:40])[C:59]([CH3:58])([CH3:54])[CH3:60]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 115237PaliperidoneHCID 516892Sodium Bicarbonate

Product 1

HCID 86711156HCID 86711156, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of Paliperidone (1.0 g, 2.34 mmol) in dichloromethane (20 mL) was treated with Boc-b-Ala-OH (443.65 mg, 2.34 mmol), dicyclohexylcarbodiimide (483.79 mg, 2.34 mmol) and N,N-dimethyl-4-pyridinamine (14.32 mg, 0.117 mmol). The reaction was stirred at room temperature under argon atmosphere. After 18 h, the reaction mixture was poured into an aqueous saturated sodium bicarbonate solution (20 mL) and the aqueous layer extracted with dichloromethane (three times 20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography (elution with dichloromethane/methanol (95/5) to give the title compound. ESI-MS (M+1) 598.

Workup

  1. extractionthe aqueous layer extracted with dichloromethane (three times 20 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (
  6. washelution with dichloromethane/methanol (95/5)

Sources & evidence

ORD record
ord-0634dd76a1524f588ecf953617399f85
Source dataset
uspto-grants-2016_07
Patent number
US09394354B2

Reaction notes

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