HCID 66849549, compound → HCID 178499353, compound

HRID 1046422Notes

Reaction equation

HRID 1046422 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:16]#[C:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:8][C:9]=1[NH:10][C@@H:11]([CH3:15])[CH2:12][CH2:13][OH:14])=[O:4].[CH3:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([C:29](Cl)=[O:30])[CH2:25][CH2:24]1>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:16]#[C:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[CH:8][C:9]=1[N:10]([C:29]([C@H:26]1[CH2:27][CH2:28][C@H:23]([CH3:22])[CH2:24][CH2:25]1)=[O:30])[C@@H:11]([CH3:15])[CH2:12][CH2:13][O:14][C:29]([C@H:26]1[CH2:27][CH2:28][C@H:23]([CH3:22])[CH2:24][CH2:25]1)=[O:30])=[O:4]

Participants

4

Reactant 2

HCID 66849549HCID 66849549, compoundHCID 178461265HCID 178461265, compound

Product 1

HCID 178499353HCID 178499353, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-(3,3-Dimethyl-but-1-ynyl)3-(3-hydroxy-1-(S)-methyl-propylamino)-thiophene-2-carboxylic acid methyl ester (4.0 g, 12.94 mmol) was taken up in pyridine (100 mL). Trans-4-methyl-cyclohexanecarbonyl chloride (12.40 g, 77.66 mmol) was added and the reaction was placed in a 100° C. preheated oil bath and stirred for 16 h. After cooling to rt the solvent was removed under reduced pressure. The residue was partitioned between EtOAc and 2N HCl(aq), the organics dried over Na2SO4, and the solids filtered. Solvent was removed under reduced pressure and 5-(3,3-dimethyl-but-1-ynyl)-3-[(trans-4-methylcyclohexanecarbonyl)-[1-(S)-methyl-3-(trans-4-methyl-cyclohexanecarbonyloxy)-propyl]-amino]-thiophene-2-carboxylic acid methyl ester (4.15 g, 58%) was isolated by silica gel chromatography as a yellow solid.

Workup

  1. customwas placed in a 100° C.
  2. customwas removed under reduced pressure
  3. customThe residue was partitioned between EtOAc and 2N HCl(aq)
  4. dry with materialthe organics dried over Na2SO4
  5. filtrationthe solids filtered
  6. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a9ae8d7b18f8488986f73bc805258ae1
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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