4-Nitrophenyl chloroformate → HCID 66915902, compound

HRID 2356968Notes

Reaction equation

HRID 2356968 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([NH2:24])[CH:22]=3)[C:17]([CH3:26])([CH3:25])[CH2:16]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:28](OC1C=CC([N+]([O-])=O)=CC=1)=[O:29].CO[C:42](=[O:58])[C:43]([CH3:57])([NH:45][CH2:46][C:47]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[N:50]=[CH:49][CH:48]=1)[CH3:44]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([N:24]4[C:42](=[O:58])[C:43]([CH3:44])([CH3:57])[N:45]([CH2:46][C:47]5[C:56]6[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=6)[N:50]=[CH:49][CH:48]=5)[C:28]4=[O:29])[CH:22]=3)[C:17]([CH3:26])([CH3:25])[CH2:16]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 21959666HCID 21959666, compoundHCID 59694308HCID 59694308, compound

Product 1

HCID 66915902HCID 66915902, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 50 mg 4-(6-amino-3,3-dimethyl-2,3-dihydro-indol-1-ylmethyl)-piperidine-1-carboxylic acid tert-butyl ester in 5 ml tetrahydrofuran 0.05 ml ethyl-diisopropylamine and 28 mg 4-nitrophenyl chloroformate were added and the mixture was stirred for 2 hours at room temperature. Afterwards 36 mg 2-methyl-2-[(quinolin-4-ylmethyl)-amino]-propionic acid methyl ester were added to the reaction mixture. After 16 hours stirring at room temperature the solvent was removed under reduced pressure and the residue was purified by preparative HPLC (C18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoroacetic acid). Lyophilization of the solution yielded a white solid.

Workup

  1. stirringAfter 16 hours stirring at room temperature the solvent
  2. customwas removed under reduced pressure
  3. customthe residue was purified by preparative HPLC (
  4. washC18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoroacetic acid)
  5. customLyophilization of the solution yielded a white solid

Sources & evidence

ORD record
ord-4af7ea443c35434ebddf9d5dbcb9bdae
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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