Sodium Bicarbonate → HCID 178499269, compound

HRID 1190055Notes

Reaction equation

HRID 1190055 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:30]2[CH2:35][CH2:34][CH2:33][CH:32]=[CH: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].C([O-])(O)=O.[Na+]>C(Cl)Cl.FC(F)(F)C(O)=O.O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:30]2[CH2:35][CH2:34][CH2:33][CH:32]=[CH:31]2)=[CH:8][C:9]=1[N:10]([C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])[CH:20]1[CH2:21][CH2:22][C:23](=[O:24])[CH2:28][CH2:29]1)=[O:4]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 178499264HCID 178499264, compound

Product 1

HCID 178499269HCID 178499269, compoundYield 87.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

A mixture of 5-cyclohex-2-enyl-3-[(1,4-dioxa-spiro[4.5]dec-8-yl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (50 mg, 0.1 mmol) in DCM (4 mL), trifluoroacetic acid (0.4 mL) and water (20 μl) was stirred for 16 h at room temperature. Trifluoroacetic acid ((0.2 mL) was added and it was stirred for another 3 h. Saturated NaHCO3 solution was added and it was extracted with DCM. The extract was washed with brine, dried over MgSO4 and evaporated yielding crude 5-cyclohex-2-enyl-3-[(trans-4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester (40 mg) which was used in the next step.

Workup

  1. stirringit was stirred for another 3 h
  2. extractionit was extracted with DCM
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-edb51278b0b24d2f9c7ede0cd6c6f848
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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