5-Chloro-2-thiophenecarboxylic acid → HCID 68685554, compound

HRID 2244688Notes

Reaction equation

HRID 2244688 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([O:10][CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH:7]([N:20]=[N+]=[N-])[CH2:6]1)=[O:4].[Cl:23][C:24]1[S:28][C:27]([C:29](O)=[O:30])=[CH:26][CH:25]=1>O=[Pt]=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C@H:8]([O:10][CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[C@@H:7]([NH:20][C:29]([C:27]2[S:28][C:24]([Cl:23])=[CH:25][CH:26]=2)=[O:30])[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 86611034HCID 86611034, compound

Product 1

HCID 68685554HCID 68685554, compound

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

In analogy to example 10A and example 1B, (S,4S)-3-azido-4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-cyclopentanecarboxylic acid methyl ester was hydrogenated in the presence of PtO2 and coupled with 5-chloro-2-thiophenecarboxylic acid to give (3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-cyclopentanecarboxylic acid methyl ester. Brown gum. MS 432.2 ([M+H]+).

Sources & evidence

ORD record
ord-90f33a30689a4e96952aac6a990b0956
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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