Water → HCID 178499289, compound

HRID 1189991Notes

Reaction equation

HRID 1189991 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:30]2(O)[CH2:35][CH2:34][C:33]([CH3:37])([CH3:36])[CH2:32][CH2:31]2)=[CH:8][C:9]=1[N:10]([CH:20]1[CH2:29][CH2:28][C:23]2(OCC[O:24]2)[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].FC(F)(F)C(O)=O.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:30]2[CH2:35][CH2:34][C:33]([CH3:36])([CH3:37])[CH2:32][CH:31]=2)=[CH:8][C:9]=1[N:10]([C:11]([C@H:13]1[CH2:14][CH2:15][C@H:16]([CH3:19])[CH2:17][CH2:18]1)=[O:12])[CH:20]1[CH2:21][CH2:22][C:23](=[O:24])[CH2:28][CH2:29]1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 178499310HCID 178499310, compound

Product 1

HCID 178499289HCID 178499289, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-[(1,4-dioxa-spiro[4.5]dec-8-yl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(1-hydroxy-4,4-dimethyl-cyclohexyl)-thiophene-2-carbo-xylic acid methyl ester (14.4 g, previous step) in dry toluene (50 mL) at room temperature was added trifluoroacetic acid (50 mL). The reaction mixture was stirred for 90 min. Water (1.28 g, 71.1 mmol) was added to the mixture and stirred for 90 min. The reaction mixture was evaporated to dryness, extracted with EtOAc and washed with saturated NaHCO3 and brine. The organic phase was dried over MgSO4, filtered and evaporated to obtain crude 5-(4,4-dimethyl-cyclohex-1-enyl)-3-[(trans-4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester (13.3 g) which was used for the next step without any purification.

Workup

  1. stirringstirred for 90 min
  2. customThe reaction mixture was evaporated to dryness
  3. extractionextracted with EtOAc
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e958d3fe6d3f45fd9b1ce6c61cac4c1d
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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