4-Methylmorpholine → HCID 53842950, compound

HRID 2050042Notes

Reaction equation

HRID 2050042 reaction equation
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.C(OC(Cl)=O)C(C)C.CN1CCOCC1.[CH3:28][S:29][CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:52])[C@H:35]([CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[N:36](C(OC(C)(C)C)=O)[CH3:37]>ClCCl>[CH3:28][S:29][CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:52])[C@H:35]([CH2:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[N:36]([C:3](=[O:5])[CH2:2][NH:1][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH3:37]

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 131711746HCID 131711746, compound

Product 1

HCID 53842950HCID 53842950, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BOC-Gly-OH (0.69 g) was dissolved in dichloromethane (10 ml) and cooled at -20°. Isobutylchloroformate (0.53 g) and NMM (0.4 g) were added with stirring. After 2 minutes Cl-H2+MePhe-NHTmp (1.2 g) and NMM (0.4 g) were added and the reaction mixture was allowed to attain room temperature. The stirring was continued for additional 3 hours when the reaction was worked up as described for (II). The dipeptide amide (IV) was obtained as a gum.

Workup

  1. temperaturecooled at -20°
  2. customto attain room temperature

Sources & evidence

ORD record
ord-40c43e357688487cab8b3d245a041b30
Source dataset
uspto-grants-1980_04
Patent number
US04199568

Reaction notes

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