1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86744085, compound

HRID 2165279Notes

Reaction equation

HRID 2165279 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:15][N:14]([O:16][CH2:17][C:18]([OH:20])=[O:19])[C:13]1=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.[CH3:33][C:34]([CH3:41])([CH3:40])[C:35]([O:37][CH2:38]I)=[O:36]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:15][N:14]([O:16][CH2:17][C:18]([O:20][CH2:38][O:37][C:35](=[O:36])[C:34]([CH3:41])([CH3:40])[CH3:33])=[O:19])[C:13]1=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 104401Iodomethyl pivalateHCID 18640041HCID 18640041, compound

Product 1

HCID 86744085HCID 86744085, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(S)-[[3-[(Benzyloxycarbonyl)amino]-2-oxo-1-azetidinyl]oxy]acetic acid (3 g; see example 79) was dissolved in 200 ml of dimethylformamide and the solution was cooled to 0° C. 1,8-diazabicyclo[5.4.0]-undec-7-ene (0.01 mol) was added followed by 2.7 g of 2,2-dimethylpropionic acid, iodomethyl ester. After 10 minutes, the mixture was diluted with 75ml of ethyl acetate, cooled (ice-water), washed with ice-cold water, ice-cold diluted sodium bicarbonate solution and again with ice-cold water. After drying (MgSO4) the filtrate was evaporated to yield 4g of the title compound, which crystallized on standing; melting point 73°-75° C.

Workup

  1. washwashed with ice-cold water, ice-cold diluted sodium bicarbonate solution and again with ice-cold water
  2. dry with materialAfter drying (MgSO4) the filtrate
  3. customwas evaporated

Sources & evidence

ORD record
ord-f1b866bc63ba49e8a26d5b418066f8ef
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

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