4-Nitrophenyl chloroformate → HCID 67301362, compound

HRID 641235Notes

Reaction equation

HRID 641235 reaction equation
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[Cl:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH2:22][C@@H:23]([OH:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:17][C:16]=1[CH3:29].[NH:30]1[CH2:35][CH2:34][CH:33]([N:36]2[CH2:42][CH2:41][C:40]3[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=3[NH:38][C:37]2=[O:47])[CH2:32][CH2:31]1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[O:47]=[C:37]1[N:36]([CH:33]2[CH2:32][CH2:31][N:30]([C:2]([O:28][C@@H:23]([C:24]([O:26][CH3:27])=[O:25])[CH2:22][C:18]3[CH:17]=[C:16]([CH3:29])[C:15]([Cl:14])=[C:20]([CH3:21])[CH:19]=3)=[O:3])[CH2:35][CH2:34]2)[CH2:42][CH2:41][C:40]2[CH:43]=[CH:44][CH:45]=[CH:46][C:39]=2[NH:38]1

Participants

6

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 67301226HCID 67301226, compound

Product 1

HCID 67301362HCID 67301362, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Under a nitrogen atmosphere 1.0 g (8.2 mmol) 4-dimethylaminopyridine in 30 mL pyridine were combined with 1.7 g (8.2 mmol) 4-nitrophenyl chloroformate, stirred for 40 min at RT, then 2.0 g (8.2 mmol) methyl (R)-3-(4-chloro-3,5-dimethyl-phenyl)-2-hydroxy-propionate were added, the mixture was again stirred for 20 min at RT and then combined with 2.0 g (8.2 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and the reaction mixture was stirred for 20 h at RT. The mixture was evaporated down i.vac., the residue was taken up in EtOAc, washed with 10% KHSO4 and saturated NaHCO3 solution and the organic phase was dried over. After the desiccant and solvent had been eliminated the residue was purified by chromatography (silica gel, cyc/EtOAc 1:1 to 1:2).

Workup

  1. stirringthe mixture was again stirred for 20 min at RT
  2. stirringthe reaction mixture was stirred for 20 h at RT
  3. customThe mixture was evaporated down i.vac
  4. washwashed with 10% KHSO4 and saturated NaHCO3 solution
  5. customthe organic phase was dried over
  6. customwas purified by chromatography (silica gel, cyc/EtOAc 1:1 to 1:2)

Sources & evidence

ORD record
ord-e90e6d5fb8f544e2aec27a7a49d898d1
Source dataset
uspto-grants-2010_04
Patent number
US07696196B2

Reaction notes

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