4-Methylmorpholine → HCID 131720287, compound

HRID 2293401Notes

Reaction equation

HRID 2293401 reaction equation
[C:1]([CH2:4][N:5]1[CH2:27][CH2:26][CH2:25][C@H:6]1[C:7]([N:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10](=[O:17])[C@H:11]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH2:12])=[O:8])(O)=[O:2].CN1CCOCC1.ClC(OCC(C)C)=O.[C:43]1([CH:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(#N)C>[C:43]1([CH:49]2[CH2:50][CH2:51][N:52]([C:1](=[O:2])[CH2:4][N:5]3[CH2:27][CH2:26][CH2:25][C@H:6]3[C:7]([N:9]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:10](=[O:17])[C@H:11]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH2:12])=[O:8])[CH2:53][CH2:54]2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 698734-PhenylpiperidineHCID 131720284L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide

Product 1

HCID 131720287HCID 131720287, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the procedure described above, a solution of L-isoleucine, N-[1-(carboxymethyl)-L-prolyl] benzylamide (0.124 g, 0.33 mmol, 1.0 eq), and N-methylmorpholine (43 uL, 40 mg, 0.40 mmol, 1.20 eq), in acetonitrile (3 mL) was treated with isobutyl chloroformate (45 uL, 47 mg, 0.35 mmol, 1.05 eq) followed by 4-phenylpiperidine (69 mg, 0.43 mmol, 1.3 eq). Workup as above provided 101 mg (59%) of L-isoleucine, N-[1-(2-(4-phenylpiperidyl)-2-oxoethyl)-L-prolyl] benzylamide.

Sources & evidence

ORD record
ord-02b5ed5e47ec4dbba68d4fee5aac59b1
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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