HCID 178461280, compound → HCID 178461281, compound

HRID 2099670Notes

Reaction equation

HRID 2099670 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][C:4]([C:8]2[S:12][C:11]([C:13]([OH:15])=[O:14])=[C:10]([N:16]([C:30]([C@H:32]3[CH2:37][CH2:36][C@H:35]([CH3:38])[CH2:34][CH2:33]3)=[O:31])[C@H:17]3[CH2:22][CH2:21][C@H:20]([O:23]C4CCCCO4)[CH2:19][CH2:18]3)[CH:9]=2)=[CH:3]1>C(O)(=O)C.C1COCC1.O>[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][C:4]([C:8]2[S:12][C:11]([C:13]([OH:15])=[O:14])=[C:10]([N:16]([C@H:17]3[CH2:18][CH2:19][C@H:20]([OH:23])[CH2:21][CH2:22]3)[C:30]([C@H:32]3[CH2:37][CH2:36][C@H:35]([CH3:38])[CH2:34][CH2:33]3)=[O:31])[CH:9]=2)=[CH:3]1

Participants

3

Reactant 1

HCID 178461280HCID 178461280, compound

Product 1

HCID 178461281HCID 178461281, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

A solution of 5-(3-hydroxy-cyclohex-1-enyl)-3-{(trans-4-methyl-cyclohexane-carbonyl)-[trans-4-(tetrahydro-pyran-2-yloxy)-cyclohexyl]-amino}-thiophene-2-carboxylic acid (4 mg, 0.007 mmol) in acetic acid:THF:H2O (4:2:1) (0.7 mL) was stirred at 45° C. for 3.5 h. The mixture was evaporated to dryness and triturated with CHCl3 and hexane yielding 5-(3-hydroxy-cyclohex-1-enyl)-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid (1.6 mg, 47%).

Workup

  1. customThe mixture was evaporated to dryness
  2. customtriturated with CHCl3 and hexane

Sources & evidence

ORD record
ord-518f69c49dd54257b6fbce75b04af981
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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