4-Nitrophenyl chloroformate → HCID 67273366, compound

HRID 730646Notes

Reaction equation

HRID 730646 reaction equation
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[CH2:14]([O:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH2:29][C@@H:30]([OH:35])[C:31]([O:33][CH3:34])=[O:32])=[CH:24][C:23]=1[CH3:36])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH:37]1[CH2:42][CH2:41][CH:40]([N:43]2[CH2:49][CH2:48][C:47]3[CH:50]=[CH:51][CH:52]=[CH:53][C:46]=3[NH:45][C:44]2=[O:54])[CH2:39][CH2:38]1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[O:54]=[C:44]1[N:43]([CH:40]2[CH2:39][CH2:38][N:37]([C:2]([O:35][C@@H:30]([C:31]([O:33][CH3:34])=[O:32])[CH2:29][C:25]3[CH:24]=[C:23]([CH3:36])[C:22]([O:21][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:27]([CH3:28])[CH:26]=3)=[O:3])[CH2:42][CH2:41]2)[CH2:49][CH2:48][C:47]2[CH:50]=[CH:51][CH:52]=[CH:53][C:46]=2[NH:45]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 67273374methyl(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-hydroxy-propionate

Product 1

HCID 67273366HCID 67273366, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Under a nitrogen atmosphere 1.93 g (9.58 mmol) 4-nitrophenyl chloroformate was added to a solution of 1.17 g (9.58 mmol) 4-dimethylaminopyridine in 50 mL pyridine, the mixture was stirred for 1.5 h at RT, combined with 3.0 g (9.58 mmol) methyl (R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-hydroxy-propionate and the mixture was stirred for 20 min at RT. Then 2.35 g (9.58 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one were added and the mixture was stirred for 20 h at RT. The reaction mixture was concentrated by evaporation i. vac., the residue was taken up in EtOAc, the organic phase was washed with 10% KHSO4 and saturated NaHCO3 solution and dried on Na2SO4. After the elimination of the desiccant and solvent the residue was purified by chromatography (silica gel, gradient Cyc/EtOAc 1:1 to 1:2).

Workup

  1. stirringthe mixture was stirred for 20 min at RT
  2. stirringthe mixture was stirred for 20 h at RT
  3. concentrationThe reaction mixture was concentrated by evaporation i
  4. washthe organic phase was washed with 10% KHSO4 and saturated NaHCO3 solution
  5. customdried on Na2SO4
  6. customAfter the elimination of the desiccant and solvent the residue was purified by chromatography (silica gel, gradient Cyc/EtOAc 1:1 to 1:2)

Sources & evidence

ORD record
ord-d1c8ce8dcdc74d88a9e77ee897cd8e07
Source dataset
uspto-grants-2009_09
Patent number
US07582625B2

Reaction notes

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