Chloroform → N-carbobenzyloxy-gamma-tert.butyl-L-glutamic acid-alpha-dimethylaminoethyl ester

HRID 1583671Notes

Reaction equation

C1([NH2+]C2CCCCC2)CCCCC1.[C:14]([NH:24][C@H:25]([C:35]([O-:37])=[O:36])[CH2:26][CH:27]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:28]([O-:30])=[O:29])([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].C1([NH2+]C2CCCCC2)CCCCC1.C(Cl)(Cl)Cl.[CH3:55][N:56]([CH2:58][CH2:59]Cl)[CH3:57]>O1CCOCC1>[CH3:55][N:56]([CH3:57])[CH:58]([O:36][C:35](=[O:37])[C@H:25]([CH2:26][CH:27]([C:31]([CH3:32])([CH3:33])[CH3:34])[C:28]([OH:30])=[O:29])[NH:24][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH3:59]

Participants

Conditions

Temperature: 70 °C

Procedure

To 1.10 g N-carbobenzyloxy-γ-tert.butyl-L-glutamic acid-dicyclohexyl ammonium salt, 1.8 ml chloroform and 1.9 ml solution of dimethylaminoethylchloride in the amount of 0.46 g, which stoichiometrically corresponds to two times molar volume, in dioxane were added to be subjected to reflux in oil bath at 70° C. for 30 hrs. After cooling down to a room temperature, said reaction mixture was similarly treated as in Step Example 1 to obtain N-carbobenzyloxy-γ-tert.butyl-L-glutamic acid-α-dimethylaminoethyl ester in the amount of 766 mg (yield; 88.4%).

Workup

additionwere added
temperatureAfter cooling down to a room temperature
customreaction mixture
additionwas similarly treated as in Step Example 1

Sources & evidence

ORD record: ord-fd8539a748c840d9bed633da305e0bea
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04552975

Reaction notes

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