Ethyl chloroformate → HCID 66603835, compound

HRID 80481Notes

Reaction equation

HRID 80481 reaction equation
CCN(C(C)C)C(C)C.Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH3:16][C:17]([CH3:51])([O:19][C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][CH:31]2[CH2:36][CH2:35][N:34]([C:37]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:38])[CH2:33][CH2:32]2)=[C:26]([C:47]([O:49][CH3:50])=[O:48])[CH:25]=1)=[O:21])[CH3:18]>C(Cl)Cl>[CH3:18][C:17]([CH3:51])([O:19][C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:31]2[CH2:36][CH2:35][N:34]([C:37]([O:39][CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[O:38])[CH2:33][CH2:32]2)=[C:26]([C:47]([O:49][CH3:50])=[O:48])[CH:25]=1)=[O:21])[CH3:16]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 66603654HCID 66603654, compound

Product 1

HCID 66603835HCID 66603835, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.08 g of DIEA and then 1.745 g of ethyl chloroformate are added to a solution of 1.6 g of benzyl 4-{[4-({[(1,1-dimethylethoxy)carbonyl]amino}methyl)-2-(methoxycarbonyl)phenyl]amino}piperidine-1-carboxylate obtained in stage 5.2 in 11 ml of DCM. The mixture is stirred at AT for 4 days. It is evaporated under reduced pressure. The residue is taken up in 10 ml of pyridine (10 ml) and 0.7 g of ethyl chloroformate is added. The mixture is stirred at AT for 4 h 00. It is evaporated under reduced pressure. The residue is chromatographed on silica gel, elution being carried out with an AcOEt/heptane mixture, (10/90, v/v) as far as (30/70, v/v), to give 0.875 g of the expected product.

Workup

  1. customIt is evaporated under reduced pressure
  2. addition0.7 g of ethyl chloroformate is added
  3. stirringThe mixture is stirred at AT for 4 h 00
  4. customIt is evaporated under reduced pressure
  5. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-77f4e90549764ff0a130c58477d8f4b3
Source dataset
uspto-grants-2014_09
Patent number
US08846654B2

Reaction notes

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