4-Methylmorpholine → HCID 86744828, compound

HRID 345758Notes

Reaction equation

ClC(O[CH2:5][CH:6]([CH3:8])[CH3:7])=O.C[N:10]1[CH2:15][CH2:14]OCC1.[CH2:16]([O:23][C:24]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O1C[CH2:34][CH2:33][CH2:32]1>>[CH2:32]([N:26]([C:24]([O:23][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:25])[CH2:27][C:28]([OH:30])=[O:29])[CH2:33][CH2:34][CH2:14][CH2:15][CH2:7][CH2:6][CH3:8].[CH2:16]([O:23][C:24]([NH:26][C@H:27]([C:28]([O-:30])=[O:29])[CH2:5][CH2:6][CH2:14][CH2:15][NH2:10])=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Reactant 4

HCID 79724-Methylmorpholine

HCID 8028Tetrahydrofuran

HCID 14349Benzyloxycarbonylglycine

HCID 62365Isobutyl chloroformate

Product 2

HCID 86744828HCID 86744828, compound

HCID 86744829HCID 86744829, compound

Procedure

The product was dissolved in 50% trifluoracetic acid in dichloromethane for 30 minutes, then evaporated, forming n-octyl Nim -benzyloxycarbonyl-L-histidyl-Ne -benzyloxycarbonyl-L-lysinate. This was dissolved in tetrahydrofuran, and isobutyl chloroformate, N-methylmorpholine and benzyloxycarbonyl-glycine were added to form n-octyl benzyloxycarbonylglycine-Nim -benzyloxycarbonyl-L-histidyl-Ne -benzyloxycarbonyl-L-lysinate. This was dissolved in glacial acetic acid and hydrogenated overnight.

Sources & evidence

ORD record: ord-b44853e23a854e4394d53687f4cd4f84
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05059588

Reaction notes

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