Dimethylformamide → HCID 86746720, compound

HRID 1452004Notes

Reaction equation

HRID 1452004 reaction equation
[C:1]([NH:4][CH2:5][S:6][CH2:7][C@@H:8]([C:10]([OH:12])=[O:11])[NH2:9])(=[O:3])[CH3:2].[CH2:13](OC(Cl)=O)[CH:14]([CH3:16])[CH3:15].CCC(O[C:26](=[O:41])[C@H:27]([CH2:36][CH2:37][C:38]([OH:40])=[O:39])[NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])C.CN(C)C=[O:45]>CN(C)C1C=CN=CC=1>[C:32]([O:31][C:29]([NH:28][C@H:27]([C:26]([NH:9][C@H:8]([C:10]([OH:12])=[O:11])[CH2:7][S:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[O:41])[CH2:36][CH:37]([O:45][C:14]([CH3:16])([CH3:15])[CH3:13])[C:38](=[O:39])[OH:40])=[O:30])([CH3:33])([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 62365Isobutyl chloroformateHCID 159010019647-70-2HCID 54145963HCID 54145963, compound

Product 1

HCID 86746720HCID 86746720, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A solution of S-(acetamidomethyl)-L-cysteine (2 mmol) 1 in 10 mL of anhydrous dimethylformamide containing 4-dimethylaminopyridine (2 mmol) is cooled in an salt-ice bath to 0°-5° C. To this solution is added previously cooled isobutylchloroformate (2 mmol), and the solution is incubated at this temperature for another 30 minutes. A solution of N-(t-butoxycarbonyl)-L-glutamic acid-γ-butyl ester 2 (2 mmol) in 5 mL of dimethylformamide is added at such a rate that the temperature of the reaction mixture does not exceed 0° C.

Workup

  1. temperatureis cooled in an salt-ice bath to 0°-5° C
  2. customdoes not exceed 0° C.

Sources & evidence

ORD record
ord-08f01376fd6b4bd0b50db41d9004f27a
Source dataset
uspto-grants-1997_02
Patent number
US05606028

Reaction notes

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