4-Methylmorpholine → rac-N-[[1-(t-butoxycarbonyl)-3-piperidinyl]-carbonyl]-beta-alanine benzyl ester

HRID 1647104Notes

Reaction equation

HRID 1647104 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C(OC)=NN=NC=1OC.CN1CCOCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:46]([O:53][C:54](=[O:58])[CH2:55][CH2:56][NH2:57])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C1COCC1>[CH2:46]([O:53][C:54](=[O:58])[CH2:55][CH2:56][NH:57][C:14]([CH:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]1)=[O:16])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 12493616Chloro-dimethoxy-triazineHCID 135021004-Methylbenzene-1-sulfonic acid--benzyl beta-alaninate (1/1)

Product 1

HCID 19926254rac-N-[[1-(t-butoxycarbonyl)-3-piperidinyl]-carbonyl]-beta-alanine benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

rac-N-(t-butoxycarbonyl)piperidine-3-carboxylic acid (Can. J. Physiol. Pharmacol. 57, 1979, 763) in THF was activated with chlorodimethoxytriazine and N-methyl-morpholine and then coupled with β-alanine benzyl ester p-toluenesulphonate (J. Org. Chem. 17, 1952, 1564) and N-methylmorpholine to give rac-N-[[1-(t-butoxycarbonyl)-3-piperidinyl]carbonyl]-β-alanine benzyl ester, m.p. 57°-59° C.

Sources & evidence

ORD record
ord-36f293389c1f46a48f833a2907022fe1
Source dataset
uspto-grants-1995_07
Patent number
US05430024

Reaction notes

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