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

HRID 1583670Notes

Reaction equation

[CH:1]1([NH2+:7][CH:8]2[CH2:13]CCCC2)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].[CH:38]1([NH2+]C2CCCCC2)CCCCC1.C(Cl)Cl>C1(C)C=CC=CC=1>[CH3:38][N:7]([CH3:1])[CH:8]([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])[CH3:13]

Participants

Conditions

Temperature: 50 °C

Procedure

To 1.20 g N-carbobenzyloxy-γ-tert.butyl-L-glutamic acid-dicyclohexyl ammonium salt, 20 ml methylene chloride and 2.1 ml solution of dimethylamioethyl-chloride in the amount of 0.5 g, which stoichiometrically corresponds to two times molar volume, in toluene were added to be subjected to reflux in oil bath at 50° C. for 35 hrs. After cooling down to the room temperature, the 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 842 mg (yield; 89.1%).

Workup

additionwere added
temperatureAfter cooling down to the room temperature
additionthe reaction mixture was similarly treated as in Step Example 1

Sources & evidence

ORD record: ord-b93ac819d9244fc395405b619a64a1a0
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04552975

Reaction notes

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