Tetrahydro-2H-thiopyran-4-carboxylic acid 1,1-dioxide → HCID 58303029, compound

HRID 587350Notes

Reaction equation

HRID 587350 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:25])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19](Cl)[CH:18]=3)[CH2:15][NH:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.[O:26]=[S:27]1(=[O:36])[CH2:32][CH2:31][CH:30]([C:33](O)=[O:34])[CH2:29][CH2:28]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:25])[N:10]([C@H:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][N:14]([C:33]([CH:30]3[CH2:31][CH2:32][S:27](=[O:36])(=[O:26])[CH2:28][CH2:29]3)=[O:34])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1491755Tetrahydro-2H-thiopyran-4-carboxylic acid 1,1-dioxideHCID 58303010HCID 58303010, compound

Product 1

HCID 58303029HCID 58303029, compound

Procedure

In analogy to the procedure described for the synthesis of example 44 (step c), the title compound [(3S,4R)-4-(4-chloro-phenyl)-1-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester was prepared from [(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester using 1,1-dioxo-hexahydro-1λ6-thiopyran-4-carboxylic acid instead of 1-methylcyclopropane-1-carboxylic acid and was obtained as an off-white foam. MS m/e: 509.1 [M]+.

Workup

  1. customIn analogy to the procedure described for the synthesis of example 44 (step c)
  2. customwas obtained as an off-white foam

Sources & evidence

ORD record
ord-105952c0804d4bcb826d607f1cff1901
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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