1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57500330, compound

HRID 501455Notes

Reaction equation

HRID 501455 reaction equation
C1CCN2C(=NCCC2)CC1.[CH2:12]([N:16]1[C:20]([C:21](SC)=[O:22])=[C:19]([CH:25]=O)[N:18]=[C:17]1[N:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]1)[C:13]#[C:14][CH3:15].[CH2:40]([O:47][C:48]([NH:50][CH:51](P(OC)(OC)=O)[C:52]([O:54][CH3:55])=[O:53])=[O:49])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>ClCCl>[CH3:55][O:54][C:52]([C:51]1[N:50]([C:48]([O:47][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)=[O:49])[C:21](=[O:22])[C:20]2[N:16]([CH2:12][C:13]#[C:14][CH3:15])[C:17]([N:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:34])[CH2:29][CH2:28]3)=[N:18][C:19]=2[CH:25]=1)=[O:53]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2734718Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetateHCID 23070991HCID 23070991, compound

Product 1

HCID 57500330HCID 57500330, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.079 g of 1,8-diazabicyclo[5.4.0]-7-undecene and then 5 ml of dichloromethane containing 0.194 g of t-butyl 4-[1-(2-butynyl)-4-formyl-5-methylsulfanylcarbonyl-1H-imidazol-2-yl]piperazine-1-carboxylate were added to a 2 ml dichloromethane solution of 0.174 g of methyl benzyloxycarbonylamino-(dimethoxyphosphoryl)-acetate, and the mixture was stirred at room temperature for 16 hours. The solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.147 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (3:2).

Workup

  1. concentrationThe solvent was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c1694b4fe0fe4d44b8433e4dddb61e84
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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