HCID 178499258, compound → HCID 178499259, compound

HRID 1190019Notes

Reaction equation

HRID 1190019 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH2:36][CH2:35][C:30]3([O:34][CH2:33][CH2:32][O:31]3)[CH2:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4]>CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:27]2[CH2:36][CH2:35][C:30]3([O:34][CH2:33][CH2:32][O:31]3)[CH2:29][CH2:28]2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:21][CH2:22][C@H:23]([OH:26])[CH2:24][CH2:25]1)[C:11]([C@H:13]1[CH2:14][CH2:15][C@H:16]([CH3:19])[CH2:17][CH2:18]1)=[O:12])=[O:4]

Participants

3

Reactant 1

HCID 178499258HCID 178499258, compound

Product 1

HCID 178499259HCID 178499259, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexane-carbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (981 mg, 1.89 mmol) in dry MeOH (30 mL) was deoxygenated by bubbling nitrogen through solution for 5 min, then 10% palladium on charcoal (202 mg) was added, nitrogen was bubbled for another 5 min, then it was displaced by hydrogen, and the mixture was stirred at room temperature overnight. The mixture was filtered through celite washing with MeOH, and filtrate was concentrated under reduced pressure to give 928 mg (95%) of crude 5-(1,4-dioxa-spiro[4.5]dec-8-yl)-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexane-carbonyl)-amino]-thiophene-2-carboxylic acid methyl ester, which was used in the following step without purification.

Workup

  1. customby bubbling nitrogen through solution for 5 min
  2. addition10% palladium on charcoal (202 mg) was added
  3. customnitrogen was bubbled for another 5 min
  4. filtrationThe mixture was filtered
  5. washthrough celite washing with MeOH, and filtrate
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-0e859bc7790b43a2a11985c8d8c520f3
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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