Diisopropylethylamine → (+)-4-Methoxymethyl-piperidine-1-carboxylic acid (7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-amide

HRID 985869Notes

Reaction equation

HRID 985869 reaction equation
C1(O[C:8](=[O:27])[NH:9][C:10]2[S:11][C:12]3[C:18]([CH:19]4[CH2:24][O:23][CH2:22][CH2:21][O:20]4)=[CH:17][CH:16]=[C:15]([O:25][CH3:26])[C:13]=3[N:14]=2)C=CC=CC=1.FC(F)(F)C(O)=O.[CH3:35][O:36][CH2:37][CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl>[O:20]1[CH2:21][CH2:22][O:23][CH2:24][CH:19]1[C:18]1[C:12]2[S:11][C:10]([NH:9][C:8]([N:41]3[CH2:42][CH2:43][CH:38]([CH2:37][O:36][CH3:35])[CH2:39][CH2:40]3)=[O:27])=[N:14][C:13]=2[C:15]([O:25][CH3:26])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 20769454(+)-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid phenyl esterHCID 225077104-Methoxymethylpiperidine trifluoroacetate

Product 1

HCID 86594663(+)-4-Methoxymethyl-piperidine-1-carboxylic acid (7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-amide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

From (+)-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid phenyl ester with 4-methoxymethyl-piperidine trifluoroacetate and N-ethyldiisopropylamine in chloroform. [α]D20=+23.0° (c=1.04, CHCl3), ES-MS m/e (%): 422 (M+H+, 100).

Sources & evidence

ORD record
ord-b2a6a83aeb2f49ddacb9b88834267b0f
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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