(3S,4R)-4-benzyloxycarbonylamino-piperidine-3-carboxylic acid ethyl ester → (3S,4R)-4-benzyloxycarbonylamino-1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidine-3-carboxylic acid ethyl ester

HRID 1019959Notes

Reaction equation

HRID 1019959 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@H:11]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].[CH3:23][O:24][C:25]1[CH:34]=[C:33]2[C:28]([N:29]=[CH:30][C:31]([S:35][CH2:36][CH:37]=O)=[N:32]2)=[CH:27][CH:26]=1>>[CH2:1]([O:3][C:4]([C@@H:6]1[C@H:11]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[CH2:10][CH2:9][N:8]([CH2:37][CH2:36][S:35][C:31]2[CH:30]=[N:29][C:28]3[C:33](=[CH:34][C:25]([O:24][CH3:23])=[CH:26][CH:27]=3)[N:32]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 66746417(3S,4R)-4-benzyloxycarbonylamino-piperidine-3-carboxylic acid ethyl esterHCID 86662002(7-Methoxy-quinoxalin-2-ylsulfanyl)-acetaldehyde

Product 1

HCID 66747494(3S,4R)-4-benzyloxycarbonylamino-1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidine-3-carboxylic acid ethyl ester

Procedure

The title compound is prepared as an off-white solid (232 mg, 70% yield) following Scheme 3 and in analogy to Example 35 using (3S,4R)-4-benzyloxycarbonylamino-piperidine-3-carboxylic acid ethyl ester (200 mg, 0.63 mmol, 1.0 eq) (prepared according to procedures described in WO2005/066176) and (7-methoxy-quinoxalin-2-ylsulfanyl)-acetaldehyde (158 mg, 0.63 mmol 1.0 eq) as starting materials.

Sources & evidence

ORD record
ord-e623d6b501dc4c1f815f2d4862b2f61d
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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