4-Nitrophenyl chloroformate → HCID 68676170, compound

HRID 491168Notes

Reaction equation

HRID 491168 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]([C:43]2[C:44](=[O:53])[NH:45][C:46]3[C:51]([CH:52]=2)=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:39][CH2:38]1>C1COCC1.N1C=CC=CC=1>[O:53]=[C:44]1[C: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)=[CH:52][C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[NH:45]1

Participants

6

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 183210463-(Piperidin-4-yl)quinolin-2(1H)-oneHCID 67273374methyl(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-hydroxy-propionate

Product 1

HCID 68676170HCID 68676170, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Under a nitrogen atmosphere 0.91 g (4.38 mmol) 4-nitrophenyl chloroformate in 10 mL THF were metered into 20 mL pyridine within 10 min at a bath temperature of 60° C., the mixture was stirred for 10 min, then 1.38 g (4.38 mmol) methyl(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-hydroxy-propionate in 40 mL pyridine were added and the reaction mixture was stirred for 2 h at 60° C. The reaction solution was combined with 1.00 g (4.38 mmol) 3-piperidin-4-yl-1H-quinoline-2-one and stirred for 4 h at 100° C. The reaction mixture was evaporated down i.vac. and the residue was purified by HPLC. The fractions containing the product were combined, evaporated down i.vac., the residue was made alkaline with 15% K2CO3 solution, the precipitate was suction filtered, washed with 20 mL water and dried at 50° C.

Workup

  1. stirringthe reaction mixture was stirred for 2 h at 60° C
  2. stirringstirred for 4 h at 100° C
  3. customThe reaction mixture was evaporated down i.vac
  4. customand the residue was purified by HPLC
  5. additionThe fractions containing the product
  6. customevaporated down i.vac
  7. filtrationfiltered
  8. washwashed with 20 mL water
  9. customdried at 50° C.

Sources & evidence

ORD record
ord-254e89b14c1140f7a0a3921ad787dd2f
Source dataset
uspto-grants-2009_05
Patent number
US07528129B2

Reaction notes

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